Lophophine

Clinical data
Other names	2C-MMDA; 2C-MMDA-1; MMDPEA; MMDPEA-1; 3-Methoxy-4,5-methylenedioxyphenethylamine; 5-Methoxy-MDPEA
Routes of; administration	Oral[1][2]
Drug class	Serotonergic psychedelic; Hallucinogen
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−1
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 ;
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Lophophine

Lophophine, also known as 2C-MMDA-1, 5-methoxy-MDPEA, or 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA or MMDPEA-1), is a psychedelic drug of the methylenedioxyphenethylamine family.[1][2][3] It is the α-demethylated homologue of MMDA, and is also closely related to mescaline (3,4,5-trimethoxyphenethylamine) and MDPEA.[1][2] Lophophine has been encountered as a novel designer drug.[3]

Use and effects

Alexander Shulgin reported in his publications that lophophine is active in the dose range of 150 to 250 mg orally.[1][2][3] 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.[1][2] Shulgin also notes that, in contrast to mescaline, lophophine causes no nausea.[1][2] He estimated that it was about twice the potency of mescaline.[1][2]

Interactions

Chemistry

Lophophine, also known as 3-methoxy-4,5-methylenedioxyphenethylamine, is a phenethylamine and methylenedioxyphenethylamine (MDxx) derivative.[1][3]

Synthesis

The chemical synthesis of lophophine has been described.[1]

Analogues

Analogues of lophophine (5-methoxy-MDPEA or 2C-MMDA-1) include mescaline (3,4,5-trimethoxyphenethylamine), 3,4-methylenedioxyphenethylamine (MDPEA), 2C-MMDA-2 (MMDPEA-2), 2C-MMDA-3a (MMDPEA-3a), and MMDA (5-methoxy-MDA), among others.[1]

Natural occurrence

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.[4]

History

Lophophine was encountered as a novel designer drug in Europe in 2023.[3]

Society and culture

Legal status

Canada

Lophophine is controlled substance in Canada under phenethylamine blanket-ban language.[5]

United States

Lophophine is not an explicitly controlled substance in the United States.[6] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

References

^ a b c d e f g h i j k A. Shulgin and A. Shulgin (1991). Pihkal. Berkeley: Transform Press. pp. 701–702.
^ a b c d e f g Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. Another compound is homomyristicylamine [lophophine (LIX)], which also has never been observed in the peyote plant, but which presents an obvious theoretical potential as a biosynthetic precursor of the tetrahydroisoquinoline alkaloids such as lophophorine and anhalonine (Kapatia et al., 1969). This compound is active in man at dosage levels of 150-200 mg, about twice the potency of mescaline (A. T. Shulgin, unpublished data, 1973). The qualitative description of its action is quite similar to that of mescaline in that there is a peaceful elevation of mood, the generation of an euphoric state, and the enhancement of visual perception, especially in the color sense. There are dissimilarities, particularly in that there is little if any nausea and there is no visual distortion. These latter differences disappear at dosages of 300 mg, and there is the generation of eyes-closed imagery similar to that observed with mescaline.
^ a b c d e "Лофофин (lophophine)". АИПСИН (in Russian). Retrieved 1 January 2026.
^ 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.
^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026

External links

[PiHKAL-1] ^ a b c d e f g h i j k A. Shulgin and A. Shulgin (1991). Pihkal. Berkeley: Transform Press. pp. 701–702.

[Shulgin1976-2] Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. Another compound is homomyristicylamine [lophophine (LIX)], which also has never been observed in the peyote plant, but which presents an obvious theoretical potential as a biosynthetic precursor of the tetrahydroisoquinoline alkaloids such as lophophorine and anhalonine (Kapatia et al., 1969). This compound is active in man at dosage levels of 150-200 mg, about twice the potency of mescaline (A. T. Shulgin, unpublished data, 1973). The qualitative description of its action is quite similar to that of mescaline in that there is a peaceful elevation of mood, the generation of an euphoric state, and the enhancement of visual perception, especially in the color sense. There are dissimilarities, particularly in that there is little if any nausea and there is no visual distortion. These latter differences disappear at dosages of 300 mg, and there is the generation of eyes-closed imagery similar to that observed with mescaline.

[Aipsin-3] "Лофофин (lophophine)". АИПСИН (in Russian). Retrieved 1 January 2026.

[pmid18720674-4] 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.

[CDSA-5] "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

[OrangeBook2026-6] Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026

Clinical data


Other names	2C-MMDA; 2C-MMDA-1; MMDPEA; MMDPEA-1; 3-Methoxy-4,5-methylenedioxyphenethylamine; 5-Methoxy-MDPEA
Routes of administration	Oral [1][2]
Drug class	Serotonergic psychedelic; Hallucinogen
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 Y
PubChem CID	90239
ChemSpider	81465 Y
UNII	C68IB79RC2
ChEMBL	ChEMBL159620 Y
CompTox Dashboard (EPA)	DTXSID80178357
ECHA InfoCard	100.041.645
Chemical and physical data
Formula	C10H13NO3
Molar mass	195.218 g·mol−1
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 Y Key:ORXQUAPZHKCCAX-UHFFFAOYSA-N Y
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