Substituted mescaline analogue Class of chemical compounds
Mescaline .A substituted mescaline analogue , also known as a scaline and typically but not always a 4-substituted 3,5-dimethoxyphenethylamine , is an analogue of the phenethylamine serotonergic psychedelic mescaline (3,4,5-trimethoxyphenethylamine).[ 1] [ 2] [ 3] [ 4] [ 5] [ 6] [ 7]
Other related compounds include the 2C (4-substituted 2,5-dimethoxyphenethylamine) and DOx (4-substituted 2,5-dimethoxyamphetamine) compounds as well as 3,4,5-trimethoxyamphetamine (TMA) and other 4-substituted 3,5-dimethoxyamphetamines (3C drugs).[ 1] [ 2] [ 3] [ 4] amphetamine rather than a phenethylamine.[ 1] [ 2] [ 3] [ 4]
The pharmacology of mescaline analogues has been studied.[ 8] [ 9] [ 10] potent than the 2C and DOx drugs.[ 1] [ 3] [ 2] receptor affinity and potency.[ 1] [ 11] [ 1] [ 3]
Substituted mescaline analogues have been extensively characterized by Alexander Shulgin and described in his books such as PiHKAL Phenethylamines I Have Known and Loved )[ 6] The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds [ 7] literature reviews .[ 1] [ 3] [ 4] [ 5] David E. Nichols [ 12] [ 13] [ 14] Daniel Trachsel ,[ 15] [ 8] [ 10]
List of substituted mescaline analogues
4-Substituted
4-D (4-trideuteromethoxy-3,5-methoxyphenethylamine)Allylescaline (AL) (4-allyloxy-3,5-dimethoxyphenethylamine)Amylescaline (4-n -amyloxy-3,5-dimethoxyphenethylamine)Benzscaline (BZ) (4-benzyloxy-3,5-dimethoxyphenethylamine)Biscaline (4-phenyl-3,5-dimethoxyphenethylamine)Buscaline (B) (4-butoxy-3,5-dimethoxyphenethylamine)Cyclopropylmescaline (CPM) (4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine)Cycloproscaline (CP) (4-cyclopropoxy-3,5-dimethoxyphenethylamine)4-Desmethylmescaline (DESMETHYL) (4-hydroxy-3,5-dimethoxyphenethylamine)4-Desoxymescaline (4-methyl-3,5-dimethoxyphenethylamine)Difluoroescaline (DFE) (multiple forms)Difluoroisoproscaline (DFIP) (multiple forms)Difluoromescaline (DFM) (4-difluoromethoxy-3,5-dimethoxyphenethylamine)Escaline (E) (4-ethoxy-3,5-dimethoxyphenethylamine)Fluoroescaline (FE) (multiple forms)Fluoromescaline (FM) (4-fluoromethoxy-3,5-dimethoxyphenethylamine)Fluoroproscaline (FP) (multiple forms)Hexylescaline (4-n -hexyloxy-3,5-dimethoxyphenethylamine)Isobuscaline (IB) (4-isobutoxy-3,5-dimethoxyphenethylamine)Isoproscaline (IP) (4-isopropoxy-3,5-dimethoxyphenethylamine)Methallylescaline (MAL) (4-methylallyloxy-3,5-dimethoxyphenethylamine)Phenescaline (4-phenylethoxy-3,5-dimethoxyphenethylamine)Propynylmescaline (4-propynyloxy-3,5-dimethoxyphenethylamine)Proscaline (P) (4-propoxy-3,5-dimethoxyphenethylamine)Septylescaline (4-n -heptyloxy-3,5-dimethoxyphenethylamine)4-Thiobuscaline (4-TB) (4-butylthio-3,5-dimethoxyphenethylamine)4-Thioescaline (4-TE) (4-ethylthio-3,5-dimethoxyphenethylamine)4-Thiomescaline (4-TM) (4-methylthio-3,5-dimethoxyphenethylamine)4-Thioproscaline (4-TP) (4-propylthio-3,5-dimethoxyphenethylamine)
3- or 5-Extended
3- or 5-Replaced
2- or 6-Substituted
2-Bromomescaline (2-bromo-3,4,5-trimethoxyphenethylamine)2-Chloromescaline (2-chloro-3,4,5-trimethoxyphenethylamine)[ 16] 2,6-Dibromomescaline (2,6-dibromo-3,4,5-trimethoxyphenethylamine)[ 17] 2,6-Dichloromescaline (2,6-dichloro-3,4,5-trimethoxyphenethylamine)[ 18] 2,3,4,5,6-Pentamethoxyphenethylamine (PeMPEA)2,3,4,5-Tetramethoxyphenethylamine (TeMPEA; TeMPEA-1)2,3,5,6-Tetramethoxyphenethylamine (TeMPEA-3)
N -Substituted
Other compounds
3,5-Dimethoxyphenethylamine (3,5-DMPEA; 4-desmethoxymescaline)Beta-D (3,4,5-trimethoxy-β-dideuterophenethylamine; β-dideuteromescaline)Bromojimscaline (1-(7-bromo-4,5,6-trimethoxy-2,3-dihydro-1H -inden-1-yl)methanamine)Bromotomscaline (1-(5-bromo-2,3,4-trimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine)Flyscaline (mescaline-FLY)Isomescaline (IM) (2,3,4-trimethoxyphenethylamine)Jimscaline (1-(4,5,6-trimethoxy-2,3-dihydro-1H -inden-1-yl)methylamine)Lophophine (3-methoxy-4,5-methylenedioxyphenethylamine)2-Thioisomescaline (2-TIM) (2-methylthio-3,4-dimethoxyphenethylamine)3-Thioisomescaline (3-TIM) (3-methylthio-2,4-dimethoxyphenethylamine)4-Thioisomescaline (4-TIM) (4-methylthio-2,4-dimethoxyphenethylamine)Tomscaline (1-(2,3,4-trimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine)
See also
References
^ a b c d e f g Shulgin AT (2003). "Basic Pharmacology and Effects" . In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook 67– 137. ISBN 978-0-12-433951-4 . Retrieved 1 February 2025 . ^ a b c d Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978). "Mescaline analogs: substitutions at the 4-position" (PDF) . NIDA Res Monogr (22): 27– 37. PMID 101882 . Archived from the original (PDF) on August 5, 2023. ^ a b c d e f Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF) . NIDA Res Monogr . 146 : 74– 91. PMID 8742795 . Archived from the original (PDF) on August 5, 2023. ^ a b c d Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships" . In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants 243– 333. doi :10.1007/978-1-4757-0510-2_6 . ISBN 978-1-4757-0512-6 ^ a b Shulgin AT (March 1973). "Mescaline: the chemistry and pharmacology of its analogs" . Lloydia . 36 (1): 46– 58. PMID 4576313 . ^ a b Alexander T. Shulgin ; Ann Shulgin (1991). PiHKAL: A Chemical Love Story ISBN 978-0-9630096-0-9 OCLC 25627628 .^ a b Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds ISBN 978-0-9630096-3-0 OCLC 709667010 . ^ a b Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2021). "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines" . Front Pharmacol . 12 : 794254. doi :10.3389/fphar.2021.794254 PMC 8865417 PMID 35222010 . {{cite journal }}: CS1 maint: article number as page number (link )^ Halberstadt AL, Chatha M, Chapman SJ, Brandt SD (March 2019). "Comparison of the behavioral effects of mescaline analogs using the head twitch response in mice" . J Psychopharmacol . 33 (3): 406– 414. doi :10.1177/0269881119826610 . PMC 6848748 PMID 30789291 . ^ a b Stoeckmann OV, Trachsel D, Liechti ME, Rudin D (21 May 2024). "Supplementum 276: Abstracts of the 8th Annual Spring Congress of the Swiss Society of General Internal Medicine: P181. New Mescaline Derivatives: Profiling of Scalines' Potency and Affinity on Different Serotonin Receptor Subtypes" . Swiss Medical Weekly . 154 (5): 138S. doi :10.57187/s.3896 ISSN 1424-3997 . ^ Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA (August 2000). "1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists" Journal of Medicinal Chemistry . 43 (16): 3074– 3084. doi :10.1021/jm9906062 . PMID 10956215 . ^ Nichols DE, Dyer DC (February 1977). "Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues". J Med Chem . 20 (2): 299– 301. doi :10.1021/jm00212a022 . PMID 836502 . ^ Monte AP, Waldman SR, Marona-Lewicka D, Wainscott DB, Nelson DL, Sanders-Bush E, Nichols DE (September 1997). "Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives". J Med Chem . 40 (19): 2997– 3008. doi :10.1021/jm970219x . PMID 9301661 . ^ McLean TH, Chambers JJ, Parrish JC, Braden MR, Marona-Lewicka D, Kurrasch-Orbaugh D, Nichols DE (July 2006). "C-(4,5,6-trimethoxyindan-1-yl)methanamine: a mescaline analogue designed using a homology model of the 5-HT2A receptor". J Med Chem . 49 (14): 4269– 4274. doi :10.1021/jm060272y . PMID 16821786 . ^ Trachsel, D.; Lehmann, D.; Enzensperger, C. (2013). Phenethylamine: von der Struktur zur Funktion Phenethylamines: From Structure to Function ]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4 OCLC 858805226 . Retrieved 31 January 2025 . ^ "PiHKAL·info" . 2-Chloromescaline . 1 April 2025. Retrieved 29 May 2025 .^ "PiHKAL·info" . Dibromomescaline . 1 April 2025. Retrieved 29 May 2025 .^ "PiHKAL·info" . 2,6-Dichloromescaline . 1 April 2025. Retrieved 29 May 2025 .
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Tryptamines: Acacia spp.Acacia acuminata Acacia confusa Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna)Dipolopterys cabrerana (chaliponga, chacruna)Mimosa tenuiflora (Mimosa hostilis ; jurema)Brosimum Brosimum acutifolium (takini)Hallucinogenic snuffs (e.g., Anadenanthera peregrina (yopo, jopo, cohoba, parica, ebene)Anadenanthera colubrina (vilca, cebil)Incilius alvarius (Bufo alvarius ; Colorado River toad, Sonoran Desert toad; bufo)Psilocybin-containing mushrooms (magic mushrooms, shrooms) (e.g., Psilocybe cubensis Psilocybe mexicana (teonanacatl)Lysergamides: Achnatherum robustum (sleepy grass)Epichloë spp.Ergot (Claviceps ) (e.g., Claviceps purpurea Claviceps paspali Morning glory (Convolvulaceae) seeds (e.g., Ipomoea tricolor (tlitliltzin, badoh negro; Ipomoea violacea )Ipomoea corymbosa (coaxihuitl, ololiúqui; Rivea Corymbosa , Turbina Corymbosa )Argyreia nervosa (Hawaiian baby woodrose; HBWR)Periglandula spp.Periglandula ipomoeae Periglandula clandestina
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2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g., 1,3-DMBA Tooltip 1,3-dimethylbutylamine , 1,4-DMAA Tooltip 1,4-dimethylamylamine , heptaminol , iproheptine , isometheptene , methylhexanamine/1,3-DMAA , octodrine , oenethyl , tuaminoheptane )Benzylamines (e.g., benzylamine , α-methylbenzylamine , MDM1EA , ALPHA , M-ALPHA , pargyline )Benzylpiperazines (e.g., benzylpiperazine , MDBZP , fipexide )Cyclohexylaminopropanes (e.g., propylhexedrine , norpropylhexedrine )Cyclopentylaminopropanes (e.g., isocyclamine , cyclopentamine )Phenoxyethylamines (e.g., 3,4,5-trimethoxyphenoxyethylamine , CT-4719 , ORG-37684 )Phenylalkenylamines (e.g., phenylbutenamine )Phenylalkynylamines (e.g., phenylbutynamine )Phenylpiperazines (e.g., 1-phenylpiperazine , mCPP Tooltip meta-chlorophenylpiperazine , TFMPP Tooltip trifluoromethylphenylpiperazine , oMPP Tooltip ortho-methylphenylpiperazine , pFPP Tooltip para-fluorophenylpiperazine , pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g., phenylpropylamine , homo-MDA , homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g., thiopropamine , methiopropamine , thiothinone )
