Anandamide - an endogenous cannabinoid neurotransmitter. I think it looks relatively easy to synthesize if one were motivated to do so from arachidonic acid (found in peanut oil) and ethanolamine.

I am wondering if there is a method, such as eating, or smoking, that would allow it to cross the blood brain barrier and give a high similiar to other cannabinoids. It seems like our body would be pretty good at metabolizing anandamide into something inactive. The effects anandamide has may be increased by taking acetaminophen. AM404 is an active metabolite of acetaminophen and has inhibits the reuptake, and metabolism of anandamide I believe.

Check out these links to get a better idea of what I am talking about:
http://en.wikipedia.org/wiki/AM404
http://en.wikipedia.org/wiki/Anandamide

Any thoughts?


EDIT:
I found a few interesting sources on anandamide being tested on rats.

D. Carriero, J.Aberman, S.Y. Lin, A. Hill, A. Makriyannis and J.D. Salamone (1998) A detailed characterization of the effects of four cannabinoid agonists on operant lever pressing. Psychopharmacol. 137: 147-156.

M.D. Aceto, S.M. Scates, R.K. Razdan, and B.R. Martin (1998) Anandamide, an Endogenous Cannabinoid, Has a Very Low Physical Dependence Potential. JPET 287: 598-605.

"In particular, the body releases an endogenous cannabinoid called anandamide, a name derived from the Sanskrit word meaning "internal bliss." When the body senses pain, anandamide binds to CB-1 and nullifies pain by blocking the signaling. However, this effect is weak and short-lived as FAAH quickly metabolizes the anandamide--the compound has a half-life of only a few minutes in vivo. " -- http://www.cannabis.net/articles/faah.html


So.. anandamide would not last very long if it were taken in a way that allowed it to be effective anyways. You'd deffinetly want a FAAH inhibitor like AM404 or something better.

I found some of the chemicals metabolized by FAAH interesting while reading the wiki page about FAAH (http://en.wikipedia.org/wiki/FAAH)

"    * Anandamide (N-arachidonoylethanolamine), an endocannabinoid[5]

    * Other N-acylethanolamines, such as N-oleoylethanolamine and N-palmitoylethanolamine[6]

    * The sleep-inducing lipid oleamide[7]

    * The N-acyltaurines, which are agonists of the transient receptor potential (TRP) family of calcium channels.[8]
"

http://en.wikipedia.org/wiki/Oleamide

Olemide, if it is a cannibinoid as some suspect, would be rediculously easy to make.

"It [Olemide] accumulates in the cerebrospinal fluid during sleep deprivation and induces sleep in animals.[2] It is being studied as a potential medical treatment for mood and sleep disorders, and cannabinoid-regulated depression.[3][4]"

... interesting huh?

Interesting. Linolamide is also active in similiar ways

http://www.ingentaconnect.com/content/els/00243205/2001/00000068/00000009/art01002

Also it seems to be being sold for an insane 50 mg for $180.00. Why so little, and for so much?  - http://www.biomol.com/core/Display.aspx?pageId=38&categoryId=806&productId=552&mid=75



Although this belongs more so in the Drug synth section, I think  Oleamide and Linolamide could be synthesized easily with decent purity from Olive oil.

Olive Oil + NaOH = Na-Fatty acids + Glycerol.

Na-Fatty Acids + HCl = NaCl + Fatty Acids.

Urea + Fatty acids =heat=> Fatty acid amides.

The fatty acids found in Olive oil consist of 50-80% Oleic acid, and 3.5-21% Linoleic acid. So you'd at least have 50% Oleamide, with some other goodies such as Linoleamide mixed in it.

I'm not to sure how one would further purify the compounds so it is just one amide of a fatty acid, but that is probably not necessary for effects. Some of the fatty acids in there might be more effective, or have other interesting pharmacological properties so that might be worth looking into.

 

I know I am just talking to myself here and double posting but here is a post from the shroomery that I found to be very valuable and would like you guys to see it here.

Studies on the sedative and hypnotic effects of oleamide in mice


   

Quote

    The hypnotic and sedative effects of oleamide (CAS 301-02-0) were studied in mice. Intraperitoneal injection of oleamide showed a time-related inhibition of the locomotor activity with the maximum effect appearing 30 min after drug administration. Oleamide, at the dose range of 43.7-700 mg/kg, dose-dependently inhibited the locomotor activity in mice. Oleamide could promote the hypnotic action induced by sodium pentobarbital. The interaction studies showed that oleamide potentiated the inhibitory effect of diazepam (CAS 439-14-5) and antagonized the stimulatory effect of ethanol, methamphetamine, and caffeine, respectively. These results provide further evidence for the hypnotic and sedative effects of oleamide, suggesting a potential therapeutic usefulness of this fatty acid amide.

Oleamide and anandamide effects on food intake and sexual behavior of rats



   

Quote

:
    Oleamide is a lipid with diverse properties, including cannabinoid-like activity. For example, it induces the classic triad of effects attributable to these molecules: decrease in core temperature, hypolocomotion, and reduction in pain perception. However, as it binds to the cannabinoid receptors (CB1) only at high concentrations, it is not considered an actual endocannabinoid. In this study, we tested the effect of oleamide on food intake and sexual behavior and compared it to the effect induced by anandamide. Results indicate that oleamide and anandamide increased food intake during the 3 h post-injection. In addition, anandamide but not oleamide induced changes in sexual performance. This study further supports the role of endocannabinoids in food ingestion and male sexual behavior and gives additional support to the notion that, although oleamide might not be an endocannabinoid, it shares some effects with them. © 2004 Elsevier Ireland Ltd. All rights reserved.

The hypnotic actions of oleamide are blocked by a camabinoid receptor antagonist


   

Quote

    THE unsaturated fatty acid amide oleamide (OA), which accumulates in the CSF of rats during sleep deprivation, induces electroencephalographically measured sleep when administered intracerebroventricularly. The mechanism of sleep induction by OA is unclear but may derive from enhancements of GABA or 5-HT receptor function, or alternatively from changes in the catabolism or uptake of the related fatty acid amide anandamide, an endogenous cannabinoid- 1 (CB1) receptor ligand. The present study tests the latter hypothesis by administering OA alone and in combination with the CB1 receptor antagonist SR141716. As previously reported, 2.8 %u03BCg OA administered intracerebroventricularly significantly shortened electroencephalographic sleep latency. SR141716 in a dose of 3 %u03BCg had no effects on sleep by itself, but when co-administered with OA prevented its sleep-inducing effects. These data suggest that at least one aspect of the hypnotic action of OA involves interactions with the CB1 receptor system, possibly by blocking the metabolism of the endogenous CB1 receptor agonist anandamide.

Isn't that interesting?

Also from bluelight:

- One such inclusion that I thought was obvious but nobody ever got was Oleamide. I would welcome the expert opinion on this one please. It is used in two mixes that I know of, and before anyone gets upset about it's use as a lubricant etc remember it's endogenous capacity as well as it's extensive, long history in the food additive industry, although maybe that industry is not such a good example.

So.. oleamide has recreational potential.

Considering the similarity between oliec acid and ricinoleic acid.. rincinoleamide might have cannabinoid activity as well.. perhaps the hydroxyl group in ricinoleic acid could be replaced by something leading to no pharmacological properties.

Hmm, interesting.
I get random drug screens so an analog as such could come in useful.

I want to bring this up because it may just be a project sometime soon. Why do you feel that urea would aminate some fatty acids Vesp. Sorry if this has been discussed but when I read this theed it was a few months ago.

Some bits on synthesizing it.

Looks easy and will be getting on it soon I believe.

Yeah, just need some pressure and some heat. Something I can't really do at the moment, but I have made some methyl oleate so I guess eventually. I seem to only have moments of interest in this compound, and then not care for a few more weeks haha

Yep I know, I don't have that at the moment haha and I haven't been willing to buy the few dollars that it is.

The metals shouldn't contaminate it much, I'd probably want to purify it anyways.

Just fyi, otto snow's book about thc and tropocaine has info about the synthesis of these...

I have attached a .txt version of this book.
 I hope that is ok.

I really want to see more on this, especially in regards to what can be made in a kitchen as opposed to a lab(which i dont have). I have heard oleamide as being only interesting as a sleep aid and not very recreational, FWIW.

p.s.
Does anyone happen to know the exact specific ingredient that is supposedly found in some of the current smoke blends? Im talking about the ones that claim to actually BE "naturally derived" (modified cacao fat, etc.) and NOT JWH/CP additives.

p.s.s
I have reason to believe, a few of the smoke blends are using some type of "naturally derived" TRPV1 agonists that somehow seem/are cannabimimetic in feel. Although i have no solid info to back this up, it is just my personal 'theory' i guess.