5-MeO-DiPT

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Template:Short description Template:Drugbox

5-MeO-DiPT, also known as 5-methoxy-N,N-diisopropyltryptamine and sometimes as foxy methoxy or simply foxy, is a psychedelic drug of the tryptamine and 5-methoxytryptamine families.[1][2][3] It is the 5-methoxy derivative of diisopropyltryptamine (DiPT).[2]

Dosage

In TiHKAL and other publications, Alexander Shulgin reported the dosage of 5-MeO-DiPT to be 6 to 12Template:Nbspmg orally, its onset to be 20 to 30Template:Nbspminutes, its time to peak effects to be 1 to 1.5Template:Nbsphours, and its duration to be 4 to 8Template:Nbsphours.[2][4][5][6] The drug can also be used intranasally.[1]

Effects

The effects of 5-MeO-DiPT are reported to include psychedelic-like effects and pro-sexual effects, among others.[2] It is said to be associated with relatively few visual changes.[2][4] Only at higher doses have closed-eye visuals occurred.[4] On the other hand, 5-MeO-DiPT is said to produce some of the auditory distortions that DiPT is associated with.[2] 5-MeO-DiPT is reported to be more like a stimulant, party drug, and sexual enhancer than a psychedelic.[3] Other effects include somatic sensual activation, talkativeness, disinhibition, emotional enhancement, easier emotional expression and communication, and intellectual activation.[4] The emotional enhancement is described as similar to that of entactogens like MDMA.[4]

Side effects

Side effects of 5-MeO-DiPT include slight mydriasis (pupil dilation) among others.[4]

Overdose

Excessive doses have caused clinical intoxication, characterized by nausea, vomiting, agitation, hypotension, mydriasis, tachycardia and hallucinations, in a number of young adults. A number of these overdoses are attributed to the drug’s extended onset of action, where first time users, who were unfamiliar with the drug, administered a second dose after initially feeling no effects. Rhabdomyolysis and renal failure occurred in one young man and another one died 3–4 hours after an apparent rectal overdose.[7] At least one death has been attributed to consumption of 5-MeO-DiPT.[8]

Interactions

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Pharmacology

Pharmacodynamics

5-MeO-DiPT activities
Target Affinity (Ki, nM)
5-HT1A 15.8–149 (Ki)
56–>10,000 (Template:Abbrlink)
94% (Template:Abbrlink)
5-HT1B 5,137
5-HT1D 1,718
5-HT1E >10,000
5-HT1F ND
5-HT2A 162–>10,000 (Ki)
6.21–946 (EC50)
99–124% (Emax)
5-HT2B 163
5-HT2C 1,740–>10,000 (Ki)
73.5–393 (EC50)
97–100% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A >10,000
5-HT6 >10,000
5-HT7 1,231
α1A >10,000
α1B >10,000
α1D ND
α2A >10,000
α2B 5,293
α2C 2,865
β1 >10,000
β2 >10,000
β3 ND
D1 >10,000
D2 >10,000
D3 >10,000
D4 >10,000
D5 >10,000
H1–H4 >10,000
M1–M5 >10,000
I1 760
σ1 9,443
σ2 3,002
Template:Abbrlink ND
Template:Abbrlink 1,618–2,531 (Ki)
646–24,215 (Template:Abbrlink)
>100,000 (EC50) (rat)
Template:Abbrlink >10,000 (Ki)
8,200–>10,000 (IC50)
>100,000 (EC50) (rat)
Template:Abbrlink >10,000 (Ki)
65,000 (IC50)
>100,000 (EC50) (rat)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [9][10][11][12][13][14][15][16]

The mechanism that produces the purported hallucinogenic and entheogenic effects of 5-MeO-DiPT is thought to result primarily from 5-HT2A receptor agonism, although additional mechanisms of action such as monoamine oxidase inhibition (MAOI) may be involved also.[17] The strongest receptor binding affinity for 5-MeO-DiPT is at the 5-HT1A receptor.[1][10][18][19]

5-MeO-DiPT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[20][18][1][21][15][19] This is blocked by serotonin 5-HT2A receptor antagonists such as volinanserin.[21][19] The drug produces a relatively weak head–twitch response, much lower in magnitude than that produced by for example 5-MeO-DMT or DOM.[15][19] 5-MeO-DiPT also produces hypolocomotion and hypothermia in rodents.[15] It partially substitutes for LSD in rodent drug discrimination tests (52–75% responding at different doses).[19] This could be completely blocked by volinanserin, whereas the serotonin 5-HT1A receptor antagonist WAY-100635 had no effect on the stimulus properties of 5-MeO-DiPT.[19]

5-MeO-DiPT is a weak serotonin reuptake inhibitor.[22][23] The elevations in serotonin levels caused by its serotonin reuptake inhibition are limited by its concomitant serotonin 5-HT1A receptor agonism, as serotonin 5-HT1A receptors serve as inhibitory autoreceptors that limit serotonin release.[22]

5-MeO-DiPT has been reported to be neurotoxic in rats.[24][25][26][1]

Pharmacokinetics

The pharmacokinetics and metabolism of 5-MeO-DiPT have been studied.[1][27][28][29]

Chemistry

Analogues of 5-MeO-DiPT include 5-MeO-DiBF, 5-MeO-DMT, 5-MeO-DPT, 5-MeO-AMT, and 5-MeO-MiPT, as well as DMT, DPT, AMT, DIPT, and MIPT, among others.

History

5-MeO-DiPT was discovered in the 1970s and was first described by Alexander Shulgin and colleagues in 1980.[3][4] It started to be encountered as a novel recreational and designer drug in 1999.[1] The drug became a controlled substance in the United States in 2003.[1]

Society and culture

File:5meodipt.jpg
5-MeO-DiPT tablets seized from Salem, Oregon.

Recreational use

Use of 5-MeO-DiPT has been found to be particularly prevalent among gay men who use drugs.[1]

Legal status

Canada

5-MeO-DiPT is not scheduled in Canada.[30]

China

As of October 2015, 5-MeO-DiPT is a controlled substance in China.[31]

Denmark

Illegal since February 2004.Script error: No such module "Unsubst".

Germany

Illegal since September 1999.Script error: No such module "Unsubst".

Greece

Illegal since February 2003.Script error: No such module "Unsubst".

Japan

Illegal since April 2005.Script error: No such module "Unsubst".

Singapore

Illegal since early 2006.Script error: No such module "Unsubst".

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 5-MeO-DiPT as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Oct 1, 2004, in their regulation SFS 2004:696 listed as 5-metoxi-N,N-diisopropyltryptamin (5-MeO-DIPT), making it illegal to sell or possess.[32]

United States

On April 4, 2003, the United States DEA added both 5-MeO-DiPT and alpha-methyltryptamine (AMT) to Schedule I of the Controlled Substances Act under "emergency scheduling" procedures. The drugs were officially placed into Schedule I on September 29, 2004. Prior to its prohibition in the U.S., 5-MeO-DiPT was sold online alongside psychoactive analogues such as DiPT, and DPT, neither of which have yet been expressly outlawed.

See also

References

Template:Reflist

External links

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  1. ↑ a b c d e f g h i Script error: No such module "Citation/CS1".
  2. ↑ a b c d e f Template:CiteTiHKAL
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  4. ↑ a b c d e f g Script error: No such module "Citation/CS1".
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  18. ↑ a b Script error: No such module "Citation/CS1".
  19. ↑ a b c d e f Script error: No such module "Citation/CS1".
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  22. ↑ a b Script error: No such module "Citation/CS1".
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  29. ↑ Script error: No such module "Citation/CS1".
  30. ↑ Script error: No such module "citation/CS1".
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  32. ↑ Script error: No such module "citation/CS1".
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