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SYNTHESIS: A solution of 100 g of 2,5-dimethoxybenzaldehyde in 220 g nitromethane was treated with 10 g anhydrous ammonium acetate, and heated on a steam bath for 2.5 h with occasional swirling. The deep-red reaction mixture was stripped of the excess nitromethane under vacuum, and the residue crystallized spontaneously. This crude nitrostyrene was purified by grinding under IPA, filtering, and air-drying, to yield 85 g of 2,5-dimethoxy-beta-nitrostyrene as a yellow-orange product of adequate purity for the next step. Further purification can be achieved by recrystallization from boiling IPA.
In a round-bottomed 2 L flask equipped with a magnetic stirrer and placed under an inert atmosphere, there was added 750 mL anhydrous THF, containing 30 g LAH. There was then added, in THF solution, 60 g 2,5-dimethoxy-beta-nitrostyrene. The final solution was a dirty yellow-brown color, and it was kept at reflux temperature for 24 h. After cooling, the excess hydride was destroyed by the dropwise addition of IPA. Then 30 mL 15% NaOH was added to convert the inorganic solids to a filterable mass. The reaction mixture was filtered and the filter cake washed first with THF and then with MeOH. The combined mother liquors and washings were freed of solvent under vacuum and the residue suspended in 1.5 L H2O. This was acidified with HCl, washed with with 3x100 mL CH2Cl2, made strongly basic with 25% NaOH, and reextracted with 4x100 mL CH2Cl2. The pooled extracts were stripped of solvent under vacuum, yielding 26 g of oily residue, which was distilled at 120-130 °C at 0.5 mm/Hg to give 21 g of a white oil, 2,5-dimethoxy-phenethylamine (2C-H) which picks up carbon dioxide from the air very quickly.
To a well-stirred solution of 24.8 g 2,5-dimethoxyphenethylamine in 40 mL glacial acetic acid, there was added 22 g elemental bromine dissolved in 40 mL acetic acid. After a couple of min, there was the formation of solids and the simultaneous evolution of considerable heat. The reaction mixture was allowed to return to room temperature, filtered, and the solids washed sparingly with cold acetic acid. This was the hydrobromide salt. There are many complicated salt forms, both polymorphs and hydrates, that can make the isolation and characterization of 2C-B treacherous. The happiest route is to form the insoluble hydrochloride salt by way of the free base. The entire mass of acetic acid-wet salt was dissolved in warm H2O, made basic to at least pH 11 with 25% NaOH, and extracted with 3x100 mL CH2Cl2. Removal of the solvent gave 33.7 g of residue which was distilled at 115-130 °C at 0.4 mm/Hg. The white oil, 27.6 g, was dissolved in 50 mL H2O containing 7.0 g acetic acid. This clear solution was vigorous stirred, and treated with 20 mL concentrated HCl. There was an immediate formation of the anhydrous salt of 2,5-dimethoxy-4-bromophenethylamine hydrochloride (2C-B). This mass of crystals was removed by filtration (it can be loosened considerably by the addition of another 60 mL H2O), washed with a little H2O, and then with several 50 mL portions of Et2O. When completely air-dry, there was obtained 31.05 g of fine white needles, with a mp of 237-239 °C with decomposition. When there is too much H2O present at the time of adding the final concentrated HCl, a hydrated form of 2C-B is obtained. The hydrobromide salt melts at 214.5-215 °C. The acetate salt was reported to have a mp of 208-209 °C.
DOSAGE: 12 - 24 mg.
DURATION: 4 - 8 h.
QUALITATIVE COMMENTS: (with 16 mg) A day at the Stanford museum. Things were visually rich, yet I felt that I was reasonably inconspicuous. The Rodin sculptures were very personal and not terribly subtle. I saw Escher things in the ceiling design, when I decided to sit in a foyer somewhere and simply pretend to rest. Walking back, the displays seen in the bark of the eucalyptus trees, and the torment and fear (of others? of themselves?) in the faces of those who were walking towards us, were as dramatic as anything I had seen in the art galleries. Our appetites were enormous, and we went to a smorgasbord that evening. A rich experience in every possible way.
(with 20 mg) The drug effect first became known to me as a shift of colors toward golden and rose tones. Pigments in the room became intensified. Shapes became rounder, more organic. A sensation of lightness and rivulets of warmth began seeping through my body. Bright lights began pulsing and flashing behind my closed lids. I began to perceive waves of energy flowing through all of us in unison. I saw all of us as a gridwork of electrical energy beings, nodes on a bright, pulsating network of light. Then the interior landscape shifted into broader scenes. Daliesque vistas were patterned with eyes of Horus, brocades of geometric design began shifting and changing through radiant patterns of light. It was an artist's paradise--representing virtually the full pantheon of the history of art.
(with 20 mg) The room was cool, and for the first hour I felt cold and chilled. That was the only mildly unpleasant part. We had been hanging crystals earlier that day, and the visions I had were dominated by prismatic light patterns. It was almost as if I became the light. I saw kaleidoscopic forms--similar to, but less intense than, when on acid--and organic forms like Georgia O'Keefe flowers, blossoming and undulating. My body was flooded with orgasms-- practically from just breathing. The lovemaking was phenomenal, passionate, ecstatic, lyric, animal, loving, tender, sublime. The music was voluptuous, almost three-dimensional. Sometimes the sound seemed distorted to me, underwater like. This was especially so for the less good recordings--but I could choose to concentrate on the beauty of the music or the inadequacy of the sound's quality, and mostly chose to concentrate on the beauty.
(with 24 mg) I am totally into my body. I am aware of every muscle and nerve in my body. The night is extraordinary--moon full. Unbelievably erotic, quiet and exquisite, almost unbearable. I cannot begin to unravel the imagery that imposes itself during the finding of an orgasm. Trying to understand physical/spiritual merging in nature --.
EXTENSIONS AND COMMENTARY: Four quotations were chosen arbitrarily from literally hundreds that have worked their ways into the files. The vast majority are positive, ranging from the colorful to the ecstatic. But not all are. There are people who choose not to go into the corporeal but, rather, prefer the out-of-body experience. They express discomfort with 2C-B, and seem to lean more to the Ketamine form of altered state, one which dissociates body from mind.
There have been reports of several overdoses that prove the intrinsic safety of this compound. Prove is used here in the classic British sense; i.e., to challenge. "The proof of the pudding is in the eating," is not a verification of quality, but an inquiry into the quality itself. (The French simplify all this by using two separate verbs for prove.) One overdose was intentional, the other accidental.
(with 64 mg) I found only mild visual and emotional effects at the 20 milligram dose, so I took the remaining 44 milligrams. I was propelled into something not of my choosing. Everything that was alive was completely fearsome. I could look at a picture of a bush, and it was just that, a picture, and it posed no threat to me. Then my gaze moved to the right, and caught a bush growing outside the window, and I was petrified. A life-form I could not understand, and thus could not control. And I felt that my own life-form was not a bit more controllable. This was from the comments of a physician who assured me that he saw no neurological concerns during this dramatic and frightening experience.
(with 100 mg) I had weighed correctly. I had simply picked up the wrong vial. And my death was to be a consequence of a totally stupid mistake. I wanted to walk outside, but there was a swimming pool there and I didn't dare fall into it. A person may believe that he has prepared himself for his own death, but when the moment comes, he is completely alone, and totally unprepared. Why now? Why me? Two hours later, I knew that I would live after all, and the experience became really marvelous. But the moment of facing death is a unique experience. In my case, I will some day meet it again, and I fear that I will be no more comfortable with it then than I was just now. This was from the comments of a psychologist who will, without doubt, use psychedelics again in the future, as a probe into the unknown.
Many of the reports that have come in over the years have mentioned the combination of MDMA and 2C-B. The most successful reports have followed a program in which the two drugs are not used at the same time, nor even too closely spaced. It appears that the optimum time for the 2C-B is at, or just before, the final baseline recovery of the MDMA. It is as if the mental and emotional discoveries can be mobilized, and something done about them. This combination has several enthusiastic advocates in the psychotherapy world, and should be the basis of careful research when these materials become legal, and accepted by the medical community.
A generalized spectrum of 2C-B action can be gleaned from the many reports that have been written describing its effects. (1) There is a steep dose response curve. Over the 12 to 24 milligram range, every 2 milligrams can make a profound increase or change of response. Initially, one should go lightly, and increase the dosage in subsequent trials by small increments. A commonly used term for a level that produces a just perceptible effect is "museum level." This is a slightly-over-threshold level which allows public activities (such as viewing paintings in a museum or scenery watching as a passenger in a car) to be entered into without attracting attention. There can be considerable discomfort associated with being in the public eye, with higher doses. (2) The 2C-B experience is one of the shortest of any major psychedelic drug. Wherever you might be, hang on. In an hour or so you will be approaching familiar territory again. (3) If there is anything ever found to be an effective aphrodisiac, it will probably be patterned after 2C-B in structure.
There are two "Tweetios" known that are related to 2C-B. (See recipe #23 for the origin of this phrase.) The 2-EtO- homologue of 2C-B is 4-bromo-2-ethoxy-5-methoxyphenethylamine, or 2CB-2ETO. The unbrominated benzaldehyde (2-ethoxy-5-methoxybenzaldehyde) had a melting point of 47.5-48.5 °C, the unbrominated nitrostyrene intermediate a melting point of 76-77 °C, and the final hydrochloride a melting point of 185-186 °C. The hydrobromide salt had a melting point of 168.5-169.5 °C. It seems that one gets about as much effect as can be had, with a dosage of about 15 milligrams, and increases above this, to 30 and to 50 milligrams merely prolong the activity (from about 3 hours to perhaps 6 hours). At no dose was there an intensity that in any way resembled that of 2C-B.
The 2,5-DiEtO- homologue of 2C-B is 4-bromo-2,5-diethoxyphenethylamine, or 2CB-2,5-DIETO. The unbrominated impure benzaldehyde (2,5-diethoxybenzaldehyde) had a melting point of about 57 °C, the unbrominated impure nitrostyrene intermediate a melting point of about 60 °C, and the final hydrochloride a melting point of 230-231 °C. The hydrobromide salt had a melting point of 192-193 °C. At levels of 55 milligrams, there was only a restless sleep, and strange dreams. The active level is not yet known.
I have been told of some studies that have involved a positional rearrangement analogue of 2C-B. This is 2-bromo-4,5-dimethoxyphenethylamine (or 6-BR-DMPEA). This would be the product of the elemental bromination of DMPEA, and it has been assayed as the hydrobromide salt. Apparently, the intravenous injection of 60 milligrams gave a rapid rush, with intense visual effects reported, largely yellow and black. Orally, there may be some activity at the 400 to 500 milligram area, but the reports described mainly sleep disturbance. This would suggest a stimulant component. The N-methyl homologue of this rearranged compound was even less active.
MERCK INDEX ENTRY
1958. 2C-B. 4-Bromo-2,5-dimethoxybenzeneethanamine; 4-bromo-2,5-dimethoxyphenethylamine; BDMPEA; alpha-desmethyl DOB; MFT; nexus. C10H14BrNO2; mol wt 260.13. C 46.17%, H 5.42%, Br 30.72%, N 5.38%, O 12.30%. Psychoactive analog of mescaline, q.v. Synthesis and activity: A. T. Shulgin, M. F. Carter, Psychopharmacol Commun. 1, 93 (1975). Qualitative analysis: F.A. Ragan, Jr. et al., J. Anal. Toxicol. 9, 91 (1985). Pharmacology: R. A. Glennon et al., Pharmacol. Biochem. Behav. 30, 597 (1988); M. Lobos et al., Gen. Pharmacol. 23, 1139 (1992).
Legality (from erowid):
USA - Schedule I - illegal in all forms without DEA license
Australia - Controlled substance and is also on the list of substances subject to import and export controls.
Estonia1 2 - Schedule Ih
Canada - Schedule III, listed as 4--bromo--2,5--dimethoxybenzeneethanamine
Japan - Scheduled in 1998
Netherlands - Scheduled as a hard drug in 1997.
Norway - Schedule II drug as of 2004
Poland - Schedule I (I-P group)
Sweden - Schedule I in 2002
Switzerland - Illegal to possess
UK -Schecule I
Last edited by Terrapinzflyer; 29-10-2010 at 03:49.
Reason: offsite links
The USA and the DEA
Nexus was first synthesized by Alexander Shulgin in the 1970s in California.
Nexus is illegal in the USA. Nexus was temporarily declared a "schedule 1 controlled substance" in 1994 and this was confirmed in 1995. Schedule 1 is most illegal that a substance can be. It means that it has no known medical use, high abuse potential, is considered dangerous to use and is generally unclean and verboten.
Ecstasy which is statistically safer than taking an airoplane flight, is schedule one. LSD, which has little or no addictive potential is also schedule one. Alcohol, which causes enormous social problems and violence, is legal. Tobacco, which is highly addictive and kills around half of it's long term users, is legal. That's drug policy for you.
"This final rule is issued by the Deputy Administrator of the Drug Enforcement Administration (DEA) to place 4-bromo- 2,5-Diethoxyphenethylamine (4-bromo-2,5-DMPEA) into Schedule I of the Controlled Substances Act (CSA). This action is based on findings made by the Deputy Administrator of the DEA, after review and evaluation of the relevant data by both DEA and the Assistant Secretary for Health, Department of Health and Human Services, that 4-bromo-2,5-DMPEA meets the statutory criteria for inclusion in Schedule I of the CSA. Since this substance has been temporarily placed in Schedule I, the regulatory controls and criminal sanctions of Schedule I will continue to be applicable to the manufacture, distribution, importation, exportation and possession of 4-bromo-2,5-DMPEA. EFFECTIVE DATE: June 2, 1995."
- US DEA
"The DEA first encountered 4-bromo-2,5-DMPEA in 1979. Since that time, several exhibits of 4-bromo-2,5-DMPEA have been analyzed by Federal and state forensic laboratories in Arizona, ---- page 28719 ---- California, Colorado, Georgia, Illinois, Iowa, Kentucky, Oregon, Pennsylvania and Texas. Clandestine laboratories producing 4- bromo-2,5-DMPEA were seized in California in 1986 and 1994 and in Arizona in 1992. It has been represented as 3,4-methylenedioxymethamphetamine (MDMA) and has been sold in adulterated sugar cubes as LSD. 4-Bromo-2,5-DMPEA has been promoted as an aphrodisiac and distributed under the product name of Nexus. DEA has seized several thousand dosage units of this product."
- US DEA
"They got wind of it in 1994. What happened apparently was that Drittewelle had a very irresponsible person doing the marketing in the USA (Florida) - for example he was setting up slot-machines in night clubs in which you could stick your money and get out a pack of Nexus.
But the thing that blew it apparently was some old geriatric fart went into a sex shop and bought a pack there. ( At that point Drittewelle was marketing the product in 10mg capsules - they later went down to 5mg caps and then 5mg tabs). Anyway, the way the story goes is that this codger reckoned that his impotency was so extreme that he obviously needed quite a few to do the trick.
Well, as you can imagine, he got himself extremely spaced and the next day phoned the FDA to complain about what was available over the counter. They started an investigation and eventually busted the importer/marketer, but they couldn't prosecute him because it wasn't illegal. So they very quickly got 2C-B made illegal - and then proceeded to try and lean on everyone else in the world to do likewise, South Africa included. Yankee doodle d*******s."
"Back on the subject of 2C-B, it might interest you to know that they were fully legal in Holland up until about two months ago (June - July 1997), when, under pressure from America's DEA, the Dutch authorities finally banned it. It had become hugely popular since they were introduced for commercial, over-the-counter sale by various commercial companies there from the beginning of last year (1996). 2C-B still remains legal in various countries (in September 1997), such as Belgium, Spain and various eastern European countries.
When 2C-B finally got banned, it had apparently began to eclipse psilocybin mushrooms in popularity. As you probably know, it is still possible to buy these mushrooms over the counter in Holland, though the authorities are under a great deal of pressure at the moment to now ban their sale.
The nickname used for the 2C-B tablets when they were available in Holland was `see-bietjies', which is a play on the letters `C-B' and translated from the Dutch means `sea-biscuits'. I imagine that much of the 2C-B that has been available in South Africa up untll recently, came directly from Holland. (So the Drittewelle product was certainly not the only one being sold and used here.)"
"... a one-time German-based company called Drittewelle (which once manufactured 2C-B under the tradename `Nexus')."
"they are a fully legal company now based in Spain. The were originally founded and based in Germany, but moved their offices to Spain after the German authorities outlawed the sale of 2C-B."
"Nexus" was Drittewelle's marketing name for 2CB, when they were selling it as an aphrodisiac. It has also found it's way onto the on black market.
The Drittewelle logo represents three breaking waves (hence the name Drittewelle which means "Third Wave" in German). Some people have noticed that the logo also seems to represent three intertwined sixes.
"Drittewelle has gone through a variety of ways of packaging their product. First it was yellow capsules, then purple tablets, and finally very small white tablets. Due to the one-time tie up between Inkwazi and Drittewelle, the product `Ubulawu Nomathotholo' came, at various times, in all three forms."
The text on the original Drittewelle packaging is given below. This is for the original 10mg yellow capsules. Check out the bit where they say that there is a side effect of "disturbances in the visual field" if the recommended dose of one capsule (10mg) is exceeded.
Clinical studies carried out in Germany have shown that cathinine - the active ingredient of NEXUS - can be effective in temporarily alleviating impotence, frigidity and diminished libido.
Cathinine is one of various phenylalkylamine compounds that have been isolated from the north African khat bush (Catha edulis) The energizing and empathogenic properties of khat are well known to the peoples of Egypt, Somalia and Kenya, who have, for centuries, been using the leaves and flowers as a tonic - as well as utilising khat for therapeutic and theurgic purposes.
The effects of NEXUS last up to 4-6 hours after ingestion. The recommended dose is one capsule taken on an empty stomach about an hour preceding the start of physical intimacy. Since the effectiveness of cathinine will diminish if used too frequently, it is advisable to take NEXUS no more than once a week.
The following side effects may occur - particularly if the recommended dose of one capsule is exceeded: disturbances in the visual field, mental confusion, increased blood pressure, rapid heart-beat, thirst and insomnia.
Driving a vehicle or undertaking any potentially hazardous activity should preferably be avoided up to six hours after taking NEXUS. It should not be used in conjunction with antidepressant drugs containing monoamine oxidase inhibitors, or within two weeks of stopping such treatment. It should not be taken during pregnancy, or by anyone suffering from high blood pressure, hypogycaemia, glaucoma, diabetes, hyperthyroidism, epilepsy or any other seizure disorder.
CLASSIFICATION: Coital analeptic (non-scheduled substance)
IDENTIFICATION AND CONTENT: 10 opaque yellow capsules each containing 10mg brominated cathinine
WARNING KEEP CAPSULES STORED IN A COOL, DRY PLACE. OUT OF REACH OF CHILDREN.
On the other side:
Supplied under licence from Drittewelle, Leipzig
Federal Republic of Germany
NEXUS is a registered trademark
Export codes: EEC-610923/US-56436
The text is somwhat misleading. 2CB is not the main ingredient in khat. Nor is it usually extracted from khat.
"certainly Drittewelle were obviously endeavouring to represent Nexus as having an organic background. The facts of the matter are that khat has many different interacting alkaloids, one of them being something called cathinine (2,5-dimethoxyphenethylamine), which is not terribly psychoactive on its own, but when brominated into 4-bromo- dimethoxy phenethylamine, aka 2C-B, it becomes a very different animal.
The main psychoactive ingredient of khat is something called cathine (norpseudoephedrine) which is now manufactured in the laboratory and is the main ingredient of a wide range of over the counter diet pills, like Thinz."
Nexus was legally sold in Southern Africa from 1993 to early 1996. It was marketed as medicine for Sangomas under the name "Ubulawu Nomathotholo".
"There seems to be a lot of confusion about this one (if Nexus is illegal in the South Africa), but a new Parliamentary bill presently in the pipeline will undoubtedly outlaw it and many other newly discovered entheogens."
Ubulawu Nomathotholo, the medicine of the singing ancestors
Sangoma is Xhosa word which is usually translated as "traditional healer". It's the African version of "shaman" or "medicine man" I suppose. However Sangomas are still a vital part of Southern African culture and are a popular alternative to Western medicine. In the bad old days a Sangoma would have been called in English a "witchdoctor". A more precise definition is `A traditional African healer who utilizes plant medicines and visionary states of consciousness to treat and heal people.'
"Ubulawu Nomathotholo was once available from Maseru, Lesotho and the name is Xhosa for "medicine of the singing ancestors". In the Xhosa shamanic tradition it was believed that when the Sangoma went into a trance, the spirits would perch on the roof beams of the hut and sing songs of knowledge down to the Sangoma. "
"It was never manufactured here, but rather in a country in Europe . A Lesotho-based herbal-remedy company called Inkwazi did a tie up with Drittewelle.
Inkwazi distributed Drittewelle's product locally under the tradename Ubulawu Nomathotholo. It was marketed from Maseru to black herbalist shops around South Africa. There was eventually a bit of a business fall-out between Inkwazi and Drittewelle with the result that Inkwazi are no longer marketing these tablets."
Although it is no longer being marketed by Inkwazi, there was a certain amount of the last packaged stocks still in circulation in South Africa in early 1997.
"I hear one of the key guys with Inkwazi is both a qualified Sangoma and a prominent member of an obscure religious group ... Just for the record, I looked up the word Inkwazi in the dictionary, it apparently means `fish eagle'."
It can appear on the street both in pressed pills and as loose powder in gel-caps. Swim has done several analyses on the content of his powder caps and has found a consistent dose of between 27-30mg. He has been rather unsuccessful analyzing pressed-pills, mostly as a result of binding agents, but judging from effects he would reckon they are on average in the same range, perhaps slightly lower, in the 23-26mg range. However, these measurements are not to be used as a guide to buying illegal drugs on the street. Unknown quantities of unknown substances could be present in almost any pill, cap, or substance bought from a street dealer and should thus be evaluated with the utmost caution and tested for purity if possible.
A friend of swims (who is an organic chem major) was able to obtain a large quantity of 2c-h (2,5 dimethoxy-4-phenethylamine) and make a vast amount of 2c-b for swim and his friends... currently it sits in swims freezer because swim doesn't like it that much.
SWIM finds that a dose of 50mg 2C-B + 600mg Pregabalin to be the sweet spot.
SWIM gets the euphoria of a typical phenethylamine, the acid-like visuals, but also a fantastically warm glowing feeling inside that differs from that of 2C-B alone. The Pregabalin definitely potentiates the 2C-B and makes everything slow right down. It also seems to generate more "graceful" visuals than 2C-B alone; CEV's become dulled in colour but vivd in fluidity. Definitely a combination SWIM recommends.
Although still available through online stores in some countries as a "research chemical" not for human consumption, 2C-B is scheduled as a drug in most jurisdictions. The following is a partial list of territories where the substance has been scheduled.
Australia: controlled and on the list of substances subject to import and export controls.
Brazil: Controlled substance, making production, distribution, or possession illegal.
Estonia: Schedule I.
Canada: CDSA Schedule III as "4-Bromo-2,5-dimethoxybenzeneethanamine and any salt, isomer or salt of isomer thereof"
Japan: Scheduled Summer 1998. Previously marketed as "Performax".
Netherlands: Scheduled on July 9th, 1997.
Norway: Schedule II as of March 22, 2004. Listed as 4-bromo-2,5-dimethoxyphenethylamine.
Poland: 2C-B is schedule I (I-P group) in Poland.
Spain: Added to Category 2 prohibited substances in 2002.
Sweden: Schedule I in Sweden on Jun 13, 2002.
Switzerland: Listed in Anhang D of the DetMV and is illegal to possess.
US: CSA Schedule I Section (d) Subsection (3) 4-Bromo-2,5-dimethoxyphenethylamine
UN: U.N. Narcotics Commission added 2C-B added to Schedule II in March 2001.
UK: All drugs in the 2C family are Class A under the 1971 Misuse of Drugs Acts which means they are illegal to produce, supply or possess in any form.
Germany: BtmG Anhang A, Illegal to produce, supply or possess in any form.
Last edited by Terrapinzflyer; 01-11-2010 at 05:02.
Reason: remove duplicate pihkal entry
Swim is interested in this drug and wants to try it orally. Should he just put it on his tongue, or take it with water? He's heard that chlorine can destroy lsd pretty easily, so he's just wondering.
Also, is there a certain dose needed to experience open eyed visuals?