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Lophophine

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries due to its similarity to mescaline and MMDA)
Identifiers
IUPAC name 2-(7-Methoxy-1,3-benzodioxol-5-yl)ethanamine
CAS Number	23693-38-1
PubChem CID	90239
ChemSpider	81465
UNII	C68IB79RC2
ChEMBL	ChEMBL159620
CompTox Dashboard (EPA)	DTXSID80178357
ECHA InfoCard	100.041.645
Chemical and physical data
Formula	C10H13NO3
Molar mass	195.218 g·mol
3D model (JSmol)	Interactive image
SMILES O1c2cc(cc(OC)c2OC1)CCN
InChI InChI=1S/C10H13NO3/c1-12-8-4-7(2-3-11)5-9-10(8)14-6-13-9/h4-5H,2-3,6,11H2,1H3 Key:ORXQUAPZHKCCAX-UHFFFAOYSA-N
(verify)

Lophophine (MMDPEA or 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. Subsequently, lophophine was indeed shown to be a minor component of both peyote and San Pedro cactus.

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.

See also

• MDPEA

References

1. ^ A. Shulgin and A. Shulgin (1991). Pihkal. Berkeley: Transform Press. pp. 701–702.
2. 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. CiteSeerX 10.1.1.689.4014. doi:10.1080/02791072.2008.10400635. PMID 18720674. S2CID 11251286.

External links

• PiHKAL: #95 Lophophine: 3-Methoxy-4,5-methylenedioxyphenethylamine
• Mescaline: The Chemistry and Pharmacology of its Analogues Archived 2014-02-16 at the Wayback Machine

• Drugs not assigned an ATC code
• Benzodioxoles
• Phenethylamines
• Phenol ethers
• Psychedelic phenethylamines
• Serotonin receptor agonists
• Phenethylamine alkaloids