Desoxy (psychedelic)

Not to be confused with desoxy- or Desoxyn.

Desoxy
Clinical data
Other namesDESOXY; 4-Desoxymescaline; 4-Deoxymescaline; 4-Methylmescaline; 4-Me-mescaline; 4-Methyl-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-methylphenethylamine; 4-Me-3,5-DMPEA
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action6–8 hours[1]
Identifiers
  • 2-(3,5-dimethoxy-4-methylphenyl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17NO2
Molar mass195.262 g·mol−1
3D model (JSmol)
  • Cc1c(cc(cc1OC)CCN)OC
  • InChI=1S/C11H17NO2/c1-8-10(13-2)6-9(4-5-12)7-11(8)14-3/h6-7H,4-5,12H2,1-3H3 checkY
  • Key:LLHRMWHYJGLIEV-UHFFFAOYSA-N checkY
  (verify)

Desoxy, or DESOXY, also known as 4-desoxymescaline, 4-methylmescaline, or 4-methyl-3,5-dimethoxyphenethylamine (4-Me-3,5-DMPEA), is a psychedelic drug of the phenethylamine and scaline families related to mescaline (3,4,5-trimethoxyphenethylamine).[1][2][3][4] It is the analogue of mescaline in which the methoxy group at the 4 position has been replaced with a methyl group, hence an oxygen has been removed and the name "desoxy".[1][2][3][4] The drug is also a positional isomer of 2C-D (4-Me-2,5-DMPEA).[1][2][3][4]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists desoxy's dose as 40 to 120 mg orally and its duration as 6 to 8 hours.[1][3][4][5] It is approximately 4-fold more potent than mescaline, which has a listed dose range of 178 to 356 mg orally as the hydrochloride salt.[3][4][1]

The effects of desoxy have been reported to include very dream-like closed-eye imagery, noteworthy closed-eye imagery with music, no open-eye visual enhancements, auditory hallucinations, sense of strangeness and the world feeling unrecognizable and alien, feeling as if one has lost their center, sleep-like trance state while trying to sleep, preservation if not enhancement of thinking skills and conversation, very good feelings, and good and mellow mood.[1] Other effects included chills or feeling cold, slight hints of neurological sensitivity, nausea, tachycardia, chest pressure, possible urinary retention, insomnia, and possible subsequent "spiritual crisis".[1]

In one report, it was said that desoxy produced a "quite fascinating experience", while in another report, it was said that "there was none of the colorful psychedelic world of mescaline" but that this "might be just around the corner", "perhaps with a larger dose", with the assessed dose of 100 mg orally being a "comfortable in-between level".[1] Higher doses than 100 mg orally were not tested.[1] According to Shulgin, removal of an oxygen atom, as with desoxy, can radically change the nature of the effects compared to mescaline.[1] In another publication, Shulgin stated that desoxy had an "activity that is difficult to classify".[4]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

Desoxy acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[6][7] Its activity values (EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy)) were 513–550 nM (83–98%) at the serotonin 5-HT2A receptor, 219 nM (100%) at the serotonin 5-HT2B receptor, and 10.5 nM (118%) at the serotonin 5-HT2C receptor.[6] The drug has been found to possess 12-fold higher affinity for the serotonin 5-HT2A receptor than mescaline (K0.5 = 67 nM and 801 nM, respectively).[7] However, it had similar activational potency though higher efficacy at the receptor compared to mescaline.[6] On the other hand, desoxy showed much greater activational potency at the serotonin 5-HT2B and 5-HT2C receptors than mescaline.[6]

Desoxy produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[6] It was about 4.4-fold more potent than mescaline in this assay and produced about 1.7-fold greater magnitude of maximal head twitches in comparison.[6]

Chemistry

Properties

Desoxy is said to have a sweet taste.[1]

Synthesis

The chemical synthesis of desoxy has been described.[1][2][8]

Analogues

Analogues of desoxy include mescaline, 4-O-desmethylmescaline (desmethyl), 4-bromomescaline (4-Br-3,5-DMPEA), 2C-D (4-Me-2,5-DMPEA), 4-Br-3,5-DMA, biscaline, and 3,4,5-trimethylphenethylamine (TMePEA; 3,4,5-tridesoxymescaline), among others.[1][2][7]

Daniel Trachsel has expressed great interest in scaline-related compounds of the formula 4-X-3,5-DMPEA without an oxygen atom at the 4 position like desoxy (4-methylmescaline; 4-Me-3,5-DMPEA) and 4-bromomescaline (4-Br-3,5-DMPEA).[5] He has described a variety of theoretical compounds of this class that could be explored, such as desoxyescaline (DE; 4-ethylmescaline; 4-Et-3,5-DMPEA), desoxytrifluoromescaline (DTFM; 4-trifluoromethylmescaline; 4-TFM-3,5-DMPEA), desoxytrifluoroescaline (DTFE; 4-trifluoroethylmescaline; 4-TFE-3,5-TMPEA), desoxyproscaline (DPR; 4-propylmescaline; 4-Pr-3,5-TMPEA), desoxyallylescaline (DAL; 4-allylmescaline; 4-AL-3,5-TMPEA), and desoxymethallylescaline (DMAL; 4-methallylmescaline; 4-MeAL-3,5-TMPEA), among others.[5]

History

Desoxy was first described in the scientific literature by F. Benington and colleagues in 1960.[2][8] Subsequently, it was described in greater detail by Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991 and other publications.[1][2]

Society and culture

Canada

Desoxy is not a controlled substance in Canada as of 2025.[9]

United States

Desoxy is not an explicitly controlled substance in the United States as of 2011.[2] However, in 1970, the Controlled Substances Act placed mescaline into Schedule I in the United States. It is similarly controlled in other nations. Depending on whether or not it is intended for human consumption, 4-desoxymescaline could be considered an analogue of mescaline, under the Federal Analogue Act and similar bills in other countries, making it illegal to manufacture, buy, possess, or distribute without a DEA or related license. In addition, DESOXY is a positional isomer of 2C-D, which makes it a Schedule I controlled substance in the United States.

See also

References

  1. ^ a b c d e f g h i j k l m n o p Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 978-0-9630096-0-9. OCLC 25627628.
  2. ^ a b c d e f g h Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. pp. 46–47. ISBN 978-0-9630096-3-0. Retrieved 2 November 2024.
  3. ^ a b c d e Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on 13 July 2025.
  4. ^ a b c d e f Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025. The removal of the oxygen atom from the 4-methoxy group of mescaline yields the compound DESOXY, which proves to have an activity that is difficult to classify.
  5. ^ a b c 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. pp. 740–744. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025. [Translated:] Compounds 154-155 contain a halogen atom instead of the 4-alkyloxy group found in many known mescaline analogues. 4-BR (154) was tested by Nichols and Dyer for the correlation between lipophilicity and 5-HT agonist activity [103]. The 3C analogue 4-BR-3,5-DMA (155) was described by Shulgin for its activity in humans [19]; at a dose of 4-10 mg, no significant effects were observed (a certain, undefined effect was present for 8-12 h), but there were indications of analgesic effects. However, these could not be confirmed in an animal study [19]. [...] Shulgin investigated the effects of desoxymescaline (DESOXY; 164) in humans [19]. He mentions a dosage of 40-120 mg and a duration of action of 6-8 hours. The psychedelic color display of mescaline (1) does not appear to be present; however, the imagery induced by music with closed eyes was clearly evident. The initial results from DESOXY (164) suggest that further interesting substances of this type are possible. What would other homo-scalines without the oxygen in the 4-position show in vitro and in vivo? The substance desoxyescalin (DE; 166) is, at least sterically speaking, closer to mescaline (1) than DESOXY (164). Many other potentially interesting deoxy compounds are conceivable, such as 167-174, and it would be quite exciting to have the in vitro and in vivo data at hand to learn more about the properties of the 3,4,5-trisubstituted phenylalkylamines. Here, too, 3C analogs would be conceivable, a currently completely unexplored class. What would happen if one of the two MeO groups in DESOXY (164) or in 166-174 were replaced by an EtO, MeS, or EtS substituent? This results in countless theoretical combinations!
  6. ^ a b c d e f Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nature Communications. 14 (1) 8221. Bibcode:2023NatCo..14.8221W. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.
  7. ^ a b c McCorvy JD (16 January 2013). Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics (Ph.D. thesis). Purdue University. Archived from the original on 15 May 2025. Retrieved 27 May 2025 – via Purdue e-Pubs.{{cite thesis}}: CS1 maint: bot: original URL status unknown (link)
  8. ^ a b Benington F, Morin R, Clark Jr L (1960). "Notes- Mescaline Analogs. X. 3,4-Dimethyl-, 3,4-Dichloro- and 3,5-Dimethoxy-4-methyl-β-phenethylamines". The Journal of Organic Chemistry. 25 (11): 2066–2067. doi:10.1021/jo01081a626. ISSN 0022-3263. Retrieved 23 November 2025.
  9. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
allikas: https://en.wikipedia.org/wiki/4-Desoxymescaline