Pentamethoxyphenethylamine

PeMPEA
Clinical data
Other names	PeMPEA; 2,3,4,5,6-Pentamethoxyphenethylamine; 2,3,4,5,6-PeMPEA
ATC code	None;
Identifiers
	IUPAC name 2-(2,3,4,5,6-pentamethoxyphenyl)ethanamine;
PubChem CID	618053;
ChemSpider	537125;
Chemical and physical data
Formula	C13H21NO5
Molar mass	271.313 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=C(C(=C(C(=C1OC)OC)OC)OC)CCN;
	InChI InChI=1S/C13H21NO5/c1-15-9-8(6-7-14)10(16-2)12(18-4)13(19-5)11(9)17-3/h6-7,14H2,1-5H3; Key:SRUXXIUKHPJJRC-UHFFFAOYSA-N;

Pentamethoxyphenethylamine (PeMPEA), also known as 2,3,4,5,6-pentamethoxyphenethylamine (2,3,4,5,6-PeMPEA), is a drug of the phenethylamine family related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine).^[1]^[2]

It has been found to produce behavioral effects in animals, with about 8-fold higher potency than mescaline in the conditioned avoidance response test.^[1]^[2]^[3]^[4]^[5] The pharmacokinetics of the drug in rodents have been studied.^[6] The effects of PeMPEA in humans have not been reported and are unknown.^[1]^[2]

It was first described in the scientific literature by 1955.^[1]^[7] PeMPEA was included as an entry in Alexander Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds.^[1]

References

^ ^a ^b ^c ^d ^e Shulgin A, Manning T, Daley PF (2011). "#108. PeMPEA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 263–264. ISBN 978-0-9630096-3-0. OCLC 709667010.
^ ^a ^b ^c Brimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97. Table 3.2.—Relative Hallucinogenic Potencies of Some Phenylethylamines [...]
^ Glennon RA, Kier LB, Shulgin AT (July 1979). "Molecular connectivity analysis of hallucinogenic mescaline analogs". Journal of Pharmaceutical Sciences. 68 (7): 906–907. doi:10.1002/jps.2600680733. PMID 458614. Previous investigators (a), employing a modified Bovet-Gatti profile, found that 2,3,4,5,6-pentamethoxyphenethylamine (XIII) is behaviorally active in animal models with a potency about eight times that of mescaline. With the relating equation, XIII is predicted to have a potency of ~4.5 mescaline units.
^ Smythies JR, Bradley RJ, Johnston VS, Benington F, Morin RD, Clark LC (1967). "Structure-activity relationship studies on mescaline. 3. The influence of the methoxy groups". Psychopharmacologia. 10 (5): 379–387. doi:10.1007/BF00403978. PMID 5588333.
^ Clark LC, Benington F, Morin RD (October 1964). "The enzymatic oxidative deamination and effect on cat behavior mescaline and structurally-related beta-phenethylamines". The Alabama Journal of Medical Sciences. 1: 417–429. PMID 14230671.
^ Cohen I, Fischer JF, Vogel WH (March 1974). "Physiological disposition of beta-phenylethylamine, 2,4,5-trimethoxyphenylethylamine, 2,3,4,5,6-pentamethoxyphenylethylamine and beta-hydroxymescaline in rat brain, liver and plasma". Psychopharmacologia. 36 (1): 77–84. doi:10.1007/BF00441384. PMID 4838506.
^ Benington F, Morin RD, Clark LC (1955). "Mescaline Analogs. II. Tetra- and Penta-Methoxy-Βeta-Phenethylamines". The Journal of Organic Chemistry. 20 (1): 102–108. doi:10.1021/jo01119a017. ISSN 0022-3263. Retrieved 3 July 2025.

External links

PeMPEA - Isomer Design

This hallucinogen-related article is a stub. You can help Wikipedia by expanding it.

[Shulgin_2011-1] Shulgin A, Manning T, Daley PF (2011). "#108. PeMPEA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 263–264. ISBN 978-0-9630096-3-0. OCLC 709667010.

[Brimblecombe_1975-2] Brimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97. Table 3.2.—Relative Hallucinogenic Potencies of Some Phenylethylamines [...]

[Glennon_1979-3] Glennon RA, Kier LB, Shulgin AT (July 1979). "Molecular connectivity analysis of hallucinogenic mescaline analogs". Journal of Pharmaceutical Sciences. 68 (7): 906–907. doi:10.1002/jps.2600680733. PMID 458614. Previous investigators (a), employing a modified Bovet-Gatti profile, found that 2,3,4,5,6-pentamethoxyphenethylamine (XIII) is behaviorally active in animal models with a potency about eight times that of mescaline. With the relating equation, XIII is predicted to have a potency of ~4.5 mescaline units.

[Smythies_1967-4] Smythies JR, Bradley RJ, Johnston VS, Benington F, Morin RD, Clark LC (1967). "Structure-activity relationship studies on mescaline. 3. The influence of the methoxy groups". Psychopharmacologia. 10 (5): 379–387. doi:10.1007/BF00403978. PMID 5588333.

[Clark_1964-5] Clark LC, Benington F, Morin RD (October 1964). "The enzymatic oxidative deamination and effect on cat behavior mescaline and structurally-related beta-phenethylamines". The Alabama Journal of Medical Sciences. 1: 417–429. PMID 14230671.

[Cohen_1974-6] Cohen I, Fischer JF, Vogel WH (March 1974). "Physiological disposition of beta-phenylethylamine, 2,4,5-trimethoxyphenylethylamine, 2,3,4,5,6-pentamethoxyphenylethylamine and beta-hydroxymescaline in rat brain, liver and plasma". Psychopharmacologia. 36 (1): 77–84. doi:10.1007/BF00441384. PMID 4838506.

[Benington_1955-7] Benington F, Morin RD, Clark LC (1955). "Mescaline Analogs. II. Tetra- and Penta-Methoxy-Βeta-Phenethylamines". The Journal of Organic Chemistry. 20 (1): 102–108. doi:10.1021/jo01119a017. ISSN 0022-3263. Retrieved 3 July 2025.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

See also

References

External links