Lophophine

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.

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
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.041.645
Chemical and physical data
FormulaC10H13NO3
Molar mass195.218 g·mol−1
3D model (JSmol)
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 Y
  • Key:ORXQUAPZHKCCAX-UHFFFAOYSA-N Y
  (verify)

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]

See also

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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.