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Methoxymethylenedioxyphenethylamine
Systematic (IUPAC) name
2-(7-methoxy-1,3-benzodioxol-5-yl)ethanamine
Identifiers
CAS number  ?
ATC code  ?
PubChem  ?
Chemical data
Formula C 10H13NO3  
Mol. mass 195.22 g/mol
Synonyms 3-methoxy-1,3-benzodioxolyl-5-ethanamine;
3-methoxy-4,5-methylenedioxy-2-phenylethylamine
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Uncontrolled
Routes Various

3-Methoxy-4,5-methylenedioxyphenethylamine (MMDPEA), also known as lophophine and homomyristicylamine, is a psychoactive drug and research chemical of the phenethylamine chemical class which acts as an entactogen, psychedelic, and stimulant, as well as an entheogen. It is the α-demethylated or phenethylamine homologue of 3-methoxy-4,5-methylenedioxyamphetamine (MMDA).

MMDPEA is also closely related on a structural level to mescaline. Notably, Alexander Shulgin ("Sasha" Shulgin) previously suggested that it may be a natural constituent of Lophophora williamsii ("Peyote"), due to it being the only logical chemical intermediate for the biosynthesis of several tetrahydroisoquinolines known to be present in the species. Subsequently, it was indeed shown to be a minor component of both Lophophora williamsii and Echinopsis pachanoi ("San Pedro").[1]

Shulgin reports that MMDPEA is active in the dosage range of 150-250 mg. He reports that at these doses, MMDPEA is very similar to mescaline in action, and that a peaceful elevation of mood, euphoria, enhancement of visual perception, and the generation of closed-eye mental imagery are all present. At dosages above 300 mg, visual distortions that resemble those of standard doses of mescaline are said to begin to appear. Shulgin also notes that in contrast to mescaline, MMDPEA causes little nausea or vomiting.

Little else is known regarding the pharmacology, pharmacokinetics, effects, and toxicity of MMDPEA.

See also

References

  1. ^ Bruhn JG, El-Seedi HR, Stephanson N, Beck O, Shulgin AT (June 2008). "Ecstasy analogues found in cacti". Journal of Psychoactive Drugs 40 (2): 219–22. PMID 18720674.  

External links


Lophophine
IUPAC name
Other names 3-Methoxy-4,5-methylenedioxyphenethylamine
2-(7-Methoxy-1,3-benzodioxol-5-yl)ethanamine
Identifiers
CAS number [1484-85-1]
SMILES
Properties
Molecular formula C10H13NO3
Molar mass 211.258 g/mol
Melting point

164-164.5 °C (hydrochloride)

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox references

Lophophine, homomyristicylamine, or 3-methoxy-4,5-methylendioxyphenethylamine is an homologue of MMDA. It is also related to mescaline and Alexander Shulgin suggested it could be a natural component in the peyote cactus because it is the only logical chemical intermediate for the biosynthesis of several of tetrahydroisoquinolines known to be present in the cactus. Subsequently it has indeed been shown to be a minor component of both Lophophora williamsii and Trichocereus pachanoi cactuses.[1] Lophophine produces hallucinogenic, psychedelic, and entheogenic effects that are similar to mescaline.

Contents

Chemistry

Lophophine is in a class of compounds commonly known as phenethylamines, and the full chemical name is 2-(7-methoxy-1,3-benzodioxol-5-yl)ethanamine.

Effects

Little is known about the psychopharmacological effects of lophophine, but it does appear to have qualitative and quantitative effects that resemble mescaline. Shulgin reports in Mescaline: The Chemistry and Pharmacology of its Analogs that lophophine is active at 150-250 mg. He states at these dosages that the action of this base is quite similar to that of mescaline; there is a peaceful elevation of mood, euphoria, enhancement of visual perception, and the generation of eyes-closed imagery. At dosages above 300 mg, visual distortions that resemble those of mescaline begin to appear. He also notes that in contrast to mescaline, little nausea is produced from lophophine ingestion.

Pharmacology

The mechanism that produces the hallucinogenic and entheogenic effects of lophophine is unknown. Although structure-activity relationships mean that it is likely to be caused by 5-HT2A receptor agonism - similar to other psychedelic drugs such as LSD and mescaline.

Dangers

The toxicity of lophophine is not known.

Legality

Lophophine is unscheduled and unregulated in the United States, however because of its close similarity in structure and effects to MDA and MMDA, possession and sale of lophophine may be subject to prosecution under the Federal Analog Act.

See also

External links

References

  1. Bruhn JG, El-Seedi HR, Stephanson N, Beck O, Shulgin AT. Ecstasy analogues found in cacti. Journal of Psychoactive Drugs. 2008 Jun;40(2):219-22. PMID 18720674







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