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Lophophine

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Title: Lophophine  
Author: World Heritage Encyclopedia
Language: English
Subject: MMDA (drug), Methylenedioxyphenethylamine, 2C-E, 2C-I, 2C-T-2
Collection: Benzodioxoles, Phenethylamines, Phenol Ethers, Psychedelic Phenethylamines, Serotonin Receptor Agonists
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Lophophine

Lophophine
Systematic (IUPAC) name
2-(7-methoxy-1,3-benzodioxol-5-yl)ethanamine
Clinical data
Pregnancy
category
  • ?
Legal status
Routes of
administration
Oral
Identifiers
CAS Registry Number  Y
ATC code None
PubChem CID:
ChemSpider  Y
ChEMBL  Y
Chemical data
Formula C10H13NO3
Molecular mass 195.22 g/mol
 Y   

Lophophine (MMDPEA, 3-methoxy-4,5-methylenedioxyphenethylamine) is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine class. It is the α-demethylated homologue of MMDA, and is also closely related to mescaline.

Alexander Shulgin originally suggested that lophophine may be a natural constituent of peyote (Lophophora williamsii) due to it being the only logical chemical intermediate for the biosynthesis of several tetrahydroisoquinolines known to be present in this cactus species.[1] Subsequently, lophophine was indeed shown to be a minor component of both peyote and San Pedro cactus.[2]

Shulgin reports that lophophine is active in the dosage range of 150–250 mg. He states that at these doses, lophophine has some similarity to mescaline in action, in producing a peaceful elevation of mood, euphoria, and mild enhancement of visual perception, but without the generation of closed-eye mental imagery. Shulgin also notes that (in contrast to mescaline), lophophine causes no nausea.[1]

At dosages above 300 mg, visual distortions that resemble those of standard doses of mescaline are said to begin to appear .

See also

References

  1. ^ a b A. Shulgin and A. Shulgin (1991). Pihkal, pp.701-702, Transform Press, Berkeley.
  2. ^ Bruhn JG, El-Seedi HR, Stephanson N, Beck O, Shulgin AT (June 2008). "Ecstasy analogues found in cacti".  

External links

  • PiHKAL: #95 Lophophine: 3-Methoxy-4,5-methylenedioxyphenethylamine
  • Psychotomimetic Drugs: Structure-Activity Relationships
  • Mescaline: The Chemistry and Pharmacology of its Analogues
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