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  #1  
Old 21-04-2009, 17:30
tantric tantric is offline
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Oleamide

Modification of 5-HT2 receptor mediated behaviour in the rat by
oleamide and the role of cannabinoid receptors



Below is from another paper...

Oleamide is an endogenous fatty acid primary amide that possesses sleep-inducing properties in animals and that has been shown to effect serotonergic receptor responses and block gap junction communication. Herein, the potentiation of the 5-HT1A receptor response is disclosed, and a study of the structural features of oleamide required for potentiation of the 5-HT2A and 5-HT1A response to serotonin (5-HT) is described. Of the naturally occurring fatty acids, the primary amide of oleic acid (oleamide) is the most effective at potentiating the 5-HT2A receptor response. The structural features required for activity were found to be highly selective. The presence, position, and stereochemistry of the Δ9-cis double bond is required, and even subtle structural variations reduce or eliminate activity. Secondary or tertiary amides may replace the primary amide but follow a well defined relationship requiring small amide substituents, suggesting that the carboxamide serves as a hydrogen bond acceptor but not donor. Alternative modifications at the carboxamide as well as modifications of the methyl terminus or the hydrocarbon region spanning the carboxamide and double bond typically eliminate activity. A less extensive study of the 5-HT1A potentiation revealed that it is more tolerant and accommodates a wider range of structural modifications. An interesting set of analogs was identified that inhibit rather than potentiate the 5-HT2A, but not the 5-HT1A, receptor response, further suggesting that such analogs may permit the selective modulation of serotonin receptor subtypes and even have opposing effects on the different subtypes.
Oleamide (1) is an endogenous fatty acid primary amide that accumulates in the cerebrospinal fluid under conditions of sleep deprivation (1–3) and induces physiological sleep in animals (1).
Consistent with its role as a prototypical member of a new class of biological signaling molecules, enzymatic regulation of the endogenous concentrations of oleamide has been described (1, 4–7) or proposed (8). Fatty acid amide hydrolase (FAAH) is an integral membrane protein that degrades 1 to oleic acid, and potent inhibitors of the enzyme have been detailed (4, 9–11). The characterization and neuronal distribution of FAAH have been disclosed (5–7), and the enzyme was found to possess the ability to hydrolyze a range of fatty acid amides including anandamide, which serves as an endogenous ligand for the cannabinoid receptor (12, 13). Unlike anandamide, an appealing feature of this new class of biological signaling agents is the primary amide, suggesting that their storage and release may be controlled in a manner analogous to that of peptide hormones terminating in a primary amide (8).
Recent studies have shown the oleamide modulates serotonergic neurotransmission (14, 15). In the first disclosure of such effects, oleamide was shown to potentiate 5-HT2C and 5-HT2A receptor-mediated chloride currents in transfected frog oocytes but not those elicited by the 5-HT3 ion-gated channel receptor or other G protein-coupled receptors (14). This potentiation was greatest for the 5-HT2C receptor subtype where the effect was observed at concentrations as low as 1 nM and was maximal at 100 nM oleamide. Oleamide did not alter the serotonin (5-HT) EC50 but instead increased receptor efficacy. Similarly, oleamide has been reported to potentiate phosphoinositide hydrolysis in rat pituitary P11 cells expressing the 5-HT2 receptor but to inhibit 5-HT7 receptor-mediated stimulation of cAMP levels in HeLa cells transfected with the receptor (15). In these efforts, oleamide was shown to act as a weak agonist at the 5-HT7 receptor but to behave as an unsurmountable antagonist in the presence of serotonin illustrating that it may act at an allosteric site. Thus, oleamide has been shown to enhance (5-HT2A, 5-HT2C), disrupt (5-HT7), or have no effect (5-HT3) on serotonergic signal transduction at various receptor subtypes. Serotonin receptors have been implicated in anxiety, depression, appetite, and thermoregulation as well as sleep and mood regulation, and strong links between 5-HT1, 5-HT2, and 5-HT7 and the regulation of sleep have been disclosed (16, 17). Herein we describe a study that defines the features of oleamide required for potentiation of the 5-HT2A receptor response and report the analogous but more tolerant potentiation of the 5-HT1A receptor, which has not been previously examined. A set of analogs that inhibit rather than potentiate the 5-HT2A, but not 5-HT1A, receptor response was identified suggesting such agents may permit selective modulation of serotonin receptor subtypes or even have opposing effects on the different subtypes.

tantric added 154 Minutes and 20 Seconds later...

As this is utterly legal, and can furthermore be made by reacting olive oil with urea, has anyone WIY bioassayed it alone?

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Interesting information about oleamide, thanks for posting it.

Last edited by tantric; 21-04-2009 at 17:30. Reason: Automerged Doublepost
  #2  
Old 22-04-2009, 23:17
runitsthepolice runitsthepolice is offline
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Re: Oleamide

Apparently this was found in some smoking blends (skunk, smoke) according to wikipedia. Other ingredients in those blends include jwh-018.
  #3  
Old 19-02-2010, 06:47
US_BLUES US_BLUES is offline
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Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

I found this strange note on the bus today, and thought I would post the note as it was written: (speculation of SWIM)

"Found some interesting information on a substance, CIS-9,10 octadecanoamide (ODA,oleamide). A new "blend" of JWH-018 and CIS-9,10 octadecanoamide (ODA,oleamide) has been noticed. This blend is being referred to as Super-G.

An article exists which hypothesizes that Oleamide can bind to the CB1 receptor. There is also some information that Oleamide was included in some of the herbal blends on the market. Is there reason to believe in the agonistic effect of Oleamide in relation to JWH varients?

Can one post one of these articles in its entireity, instead of linking it?"

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Thanks for bringing this to our attention
  #4  
Old 28-02-2010, 04:21
skunkjar skunkjar is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

Well no articles, but SWIMMY has heard first hand reports that it is in fact active

Quote:
50mg Oleamide + 50mg Stearamide + 800mg soy lecithin mixed together in 2 capsules.

TOO MUCH!

20mg of each would be much better.

Gulliver was spinning, dizzy, seeing color flashes, "light rain" cev's, euphoria(but blocked by nausea as Gulliver had TOO MUCH).

WOW! The addition of lecithin put it in OVERDRIVE! Prior suggestions of upwards of 100mg are NO LONGER SUGGESTED!

Also, Oleamide has a 'cannabinoid' like feel.
Stearamide does not really have any 'cannabinoid' like feel, but is physically euphoric in a almost 'new' way(not amp/opi/canna like euphoria, unique!).
SWIMMY is in the process of aquiring some of these novel fatty acid amides. He says he will keep us informed.

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Great idea, very helpful
  #5  
Old 28-02-2010, 06:19
msimm msimm is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

Just because I was confused a moment when I tried looking Stearamide up:

 CASSynonyms:Possible Dose - via skunkjar
Stearamide124-26-5Octadecanamide, Stearamide, Octadecylamide, Stearoylamide, Stearoylamine, Octadecamide, Stearylamide, Stearic amide, Kemamide S, Adogen 42, Stearic Acid Amide, Amide C1820 mg #2
Oleamide301-02-0Oleamide, Oleylamide, Oleic acid amide, Oleyl amide, Adogen 73, Crodamide O, Slip-eze, Crodamide OR, Armoslip CP, 9-Octadecenamide, 9Z-octadecenamide, 9-Octadecenamide20 mg #2
Erucamide #4204-009-2Erucylamide, Erucyl amide, 13-Docosenamide, Erucic acid amide, ERUCAMIDE, 13-DocosenamideND

Interesting stuff. Especially if they are orally active at such reasonably low doses.

Last edited by msimm; 28-02-2010 at 07:30. Reason: Added Erucamide, mentioned by skunkjar below.
  #6  
Old 28-02-2010, 07:13
skunkjar skunkjar is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

SWIMMY is getting some:

Oleamide (Damned nice according to Gulliver)
Stearamide (Gulliver's favorite)
Erucamide (untested by Gulliver)

Anyone have any info on these?
  #7  
Old 28-02-2010, 12:45
Drats Gold member Drats is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

Hm SWIM is wondering about Oleamide, cause there was the warning of industrial Oleamide in several blends like "Smoke". So is Oleamid dangerous or was it just dangerous cause it was industrial Oleamide which had been used in those blends?

But on the other hand, SWIM also seen on Wikipedia that it would have intoxicating effects. Or was it just the fact that the Oleamide was smoked through those blends?

SWIM doesn´t think this is Off-topic in that case, cause the side effects of such a "new" thing should be also considered and discussed.
  #8  
Old 28-02-2010, 17:06
msimm msimm is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

Swim doesn't know the answer to swiy question, but if Smoke was an example of such a blend the hazard might have been to the tissue of the lungs. The smoke could be caustic and often large hits would lead to coughing fits that themselves felt damaging. Nasty.

A clip from the MSDS for Stearamide:

Quote:
Potential Health Effects
Eye: Dust may cause mechanical irritation.
Skin: May cause skin irritation.
Ingestion: May cause digestive tract disturbances. The toxicological properties of this substance have not been fully investigated.
Inhalation: May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic: No information found.
From a Oleamide MSDS:

Quote:
Health Hazards (Acute and Chronic):
Contact with this product may cause drowsiness. The toxicological properties of this compound have not been fully
And Erucamide:
Quote:
Irritant: Irritating to eyes, respiratory system and skin.

In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

Wear suitable protective clothing.
All seem to be called irritants and suggest the use of respirators and protective clothing when handling but none seem to describe it as acutely toxic or provide toxicological data.

Last edited by msimm; 28-02-2010 at 17:19.
  #9  
Old 28-02-2010, 22:03
skunkjar skunkjar is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

As with most other research chemicals there have probably not been many if any toxicology studies... But Gulliver and Swimmy feel that researching these is interesting enough to warrant the risk involved. Also many people regularly ingest substances that are skin and respiratory irritants, like hot chilli's and various other spices.

There is also an entheogen vendor selling other fatty acid amides - NAPE isolates that are reported to have pretty enjoyable effects when vaped or taken orally.

This seems to be a pretty unexplored class of chemicals, it is interesting to watch Swimmy doing some of the inital research IMHO.

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Thanks for sharing this skunkjar, keep the info coming!
  #10  
Old 03-03-2010, 20:22
hX_ hX_ is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

Found this article.

mod edit link just led to the abstract- attached below as text file. link to full file didn't work.

we also have a paper on oleamide: Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems. in the file archives

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great contribution
Attached Files
File Type: txt pubmed_result-1.txt (2.3 KB, 18 views)

Last edited by Terrapinzflyer; 03-03-2010 at 21:49.
  #11  
Old 11-03-2010, 05:52
fnord fnord is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

Quote:
My grandma find that oleamide potentates JWH's as well as marijuana and would assume that this is the real reason its included in the blends. Grandma also finds that steromide and euricimide mixed in a 25/25/25mg oral dose combined with 700mg of soy lechtin to be very heady and euphoric especially when mixed with a little pot.

From my grannies studies this is added to potentate JWH's and it also give a mild buzz on its own.
Double posted by request.
  #12  
Old 12-03-2010, 20:04
bluntshell bluntshell is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

Quote:
Originally Posted by skunkjar View Post
There is also an entheogen vendor selling other fatty acid amides - NAPE isolates that are reported to have pretty enjoyable effects when vaped or taken orally.

This seems to be a pretty unexplored class of chemicals, it is interesting to watch Swimmy doing some of the inital research IMHO.
A thread about this http://www.drugs-forum.com/forum/sho...845#post781845

bluntshell added 5 Minutes and 26 Seconds later...

Quote:
Originally Posted by US_BLUES View Post

"Found some interesting information on a substance, CIS-9,10 octadecanoamide (ODA,oleamide). A new "blend" of JWH-018 and CIS-9,10 octadecanoamide (ODA,oleamide) has been noticed. This blend is being referred to as Super-G.

SWIM tried this product. He said it's effect was similar to that of JWH-018 alone, but when smoked on top of ash or plant matter or vaped, it burned the lungs. SWIM also said the high was a little more physically numbing or more medicinal than jwh-018 alone.

Last edited by bluntshell; 12-03-2010 at 20:04. Reason: Automerged Doublepost
  #13  
Old 12-03-2010, 20:35
msimm msimm is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

Quote:
Originally Posted by fnord View Post
My grandma find that oleamide potentates JWH's as well as marijuana and would assume that this is the real reason its included in the blends. Grandma also finds that steromide and euricimide mixed in a 25/25/25mg oral dose combined with 700mg of soy lechtin to be very heady and euphoric especially when mixed with a little pot.

From my grannies studies this is added to potentate JWH's and it also give a mild buzz on its own.
You mention your grandma mixes 25/25/25mg but only mention steromide and euricimide I might updated the chart (if that helps anyone) if I knew which three you meant (presumable Oleamide is the one grandma left off?).

Anyway, super interesting discussion.
  #14  
Old 15-03-2010, 19:06
fnord fnord is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

Quote:
Originally Posted by msimm View Post
You mention your grandma mixes 25/25/25mg but only mention steromide and euricimide I might updated the chart (if that helps anyone) if I knew which three you meant (presumable Oleamide is the one grandma left off?).

Anyway, super interesting discussion.
Correct. My grandma keeps hering about lung/throat irataion but she nor her guinie pigs has not noticed this at all. even after at least 10~ grams in the past week and a half.
  #15  
Old 13-04-2012, 01:11
rannyfash rannyfash is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

swim told me how easy they are to make from everyday stuff, get your oil, boil it with ammonia, get the white solid and sublime (evapourate and crystalise), although it makes sense i dont trust this particular swim that much

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This makes no sense, and borders on synthesis discussion which isnt allowed outside of the chem forums
  #16  
Old 30-11-2012, 23:42
Rob Cypher Rob Cypher is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

Um; is this stuff orally active (or is lechtin needed to help with that process)? Smoking it doesn't sound too smart to me.

From a wiki (I know, not the best source but the sources in the article check out): "Oleamide was found by researchers to be leaking out of polypropylene plastics used in laboratory experiments, affecting experimental results. Since polypropylene is used in a wide number of food containers such as those for yogurt, the problem is being studied. A chemical analysis of 44 products containing synthetic cannabinoid drugs marketed as "herbal incense" revealed oleamide in 7 of the products tested."

(the article regarding the lab accidents)

Quote:
Medical researchers at the University of Alberta say that two chemicals leaking from plastic laboratory equipment were so biologically active they ruined a drug experiment. The inadvertent discovery could have wide-ranging consequences because the chemicals causing the experiment to go awry were leaching from polypropylene, one of the most commonly used plastics in the world. Besides being found in scientific equipment, the plastic is used to make everything from yogurt tubs to clothing. The findings were so alarming to the researchers, from the university's faculty of medicine, that they issued a warning yesterday in the journal Science, alerting others scientists to the possibility that contaminants from plastic ware in their laboratories could put experiments at risk. Not enough is known about the two substances leaking from the plastic - quaternary ammonium biocides and oleamide - to know what hazard, if any, they might pose through exposure to consumer products made from polypropylene.

"It's very difficult to say whether we should be worried from a health point of view about this," said Andrew Holt, the paper's lead researcher and an assistant professor of pharmacology. But Dr. Holt said that virtually all medical laboratories in the world routinely use materials, such as bottles and tubing, made from the polypropylene, putting their results at risk. "Scientists need to be aware of this," Dr. Holt said.

Other experts, though, said they were worried that plastics might be leading to human exposures, with unknown effects. "We simply don't want these chemicals getting into our bodies," said Rebecca Sutton, senior scientist with Environmental Working Group, a U.S.-based advocacy organization. The group wrote to the U.S. Environmental Protection Agency last month, objecting to an effort to loosen exposure standards for quaternary ammonium compounds.

The Alberta researchers aren't the first to be surprised that chemicals inadvertently leaking from some types of plastic can skew experimental results. During the early 1990s, researchers at Stanford University School of Medicine in California found that bisphenol A leaking from a different type of plastic, polycarbonate, caused experiments investigating estrogen to run amok. Their discovery helped trigger a flurry of research into the chemical. Last month, Health Canada said it would place bisphenol A, which is now considered a female hormone mimic, on the country's list of toxic substances.

At the U of A, a team lead by Dr. Holt made their discovery while conducting experiments on a human enzyme that is the target for drugs to treat Parkinson's disease. The researchers were trying to inhibit the activity of the enzyme with ammonium chloride. They were surprised to find that even when they only added one part per million of the ammonium chloride, an amount that is so minute it was expected to have little effect, some mystery substance was still blocking the enzyme function.

The team initially suspected contaminants in the chemicals they were using, but eventually they determined that biologically active substances were leaking from the plastic tubes they used to transfer liquids in the experiment. Using sophisticated testing equipment, they found that one of the mystery chemicals was oleamide, a compound used to improve the fluidity of molten plastic. Oleamide also occurs naturally in the human body, and is found in the brain and blood. The chemical is also added to other types of plastic, such as polyvinyl chloride and low-density polyethylene.

Ms. Sutton expressed concern that exposing people to extra oleamide might alter brain function. "If we end up dosing ourselves with higher levels, this could disrupt various processes."

http://www.ewg.org/news/researchers-...common-plastic
All that being said; I don't get the idea that this is really toxic by itself, but the above is just a bit of interesting trivia to consider.
  #17  
Old 01-02-2013, 22:43
LostMagic LostMagic is offline
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Oleamide in a blend :p

my cousin got this incense product that tried to sound all fancy and organic. then there was one little thing that caught his attention Contains fatty acid amides from Olive Oil Obviously upon further research, oleamide appears to be an important factor in this blend. And he says this because he opened it up and there are white flakes all over the damn blend!

Anyway he orally ingested some of this corrosive material and a half hour later his eyes are bloodshot and he feels a little spacy. In his opinion, it seems pretty peripheral.

Just a heads up, if your herbal blend says it has fatty acid amides, it could be oleamide and that stuff is corrosive.
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Old 04-02-2013, 11:08
rannyfash rannyfash is offline
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

If its corrosive you could just neutralise it with a corresponding acid to make a salt for oral use
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Old 05-02-2013, 01:01
DrBD DrBD is offline
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Re: Oleamide in a blend :p

Quote:
Originally Posted by LostMagic View Post
Just a heads up, if your herbal blend says it has fatty acid amides, it could be oleamide and that stuff is corrosive.
LOL. No.

Synthetically produced oleamide has a variety of industrial uses including as a slip agent, a lubricant, and a corrosion inhibitor.
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Old 07-04-2013, 17:18
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Re: Oleamide - agonist on the CB1 receptor? CIS-9,10 octadecanoamide (ODA,oleamide)

Up to 1g and more of oleamide and startamide with soy lecithin. No effects except plastic taste.

Any suggestions or good experience with this from anyone?

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drugs, herbal incense, oleamide, pharmacology, pharmacology info, pharmacology information

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