Wikipedia

5-MeO-pyr-T

5-MeO-pyr-T (5-methoxy-N,N-tetramethylenetryptamine) is a lesser-known psychedelic drug. It is the 5-methoxy analog of pyr-T. 5-MeO-pyr-T was first synthesized by Hunt & Brimblecombe,[1] who credited S. Mitzal for characterization of chemical properties.[2] Later human tests were reported by Alexander Shulgin, in his book TiHKAL. An oral dosage of 0.5 to 2 mg, and an inhaled dosage of 2–3 mg are reported. 5-MeO-pyr-T causes varying reactions, such as amnesia, tinnitus, vomiting, and a 5-MeO-DMT-like rushing sensation. At the highest dosage reported in TiHKAL, the subject describes awakening from an apparent fugue state during which they were wandering the streets, with complete amnesia upon awakening.[3]

5-MeO-pyr-T
Names
IUPAC name
5-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole
Other names
  • 5-Methoxy-N,N-tetramethylenetryptamine
  • Indole, 5-methoxy-3-[2-(1-Pyrrolidyl)-Ethyl]
  • 1-[2-(5-Methoxy-1H-indol-3-yl)ethyl]pyrrolidine
  • "Pyrrolidyl-5-methoxy-tryptamine"
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C15H20N2O/c1-18-13-4-5-15-14(10-13)12(11-16-15)6-9-17-7-2-3-8-17/h4-5,10-11,16H,2-3,6-9H2,1H3 checkY
    Key: KAASYKNZNPWPQG-UHFFFAOYSA-N checkY
  • InChI=1/C15H20N2O/c1-18-13-4-5-15-14(10-13)12(11-16-15)6-9-17-7-2-3-8-17/h4-5,10-11,16H,2-3,6-9H2,1H3
    Key: KAASYKNZNPWPQG-UHFFFAOYAA
  • O(c3ccc1c(c(c[nH]1)CCN2CCCC2)c3)C
Properties
C15H20N2O
Molar mass 244.338 g·mol−1
Appearance Off-white oil
Density 200.3g/cm3
Melting point 164 to 167 °C (327 to 333 °F; 437 to 440 K) Melting point given for hydrochloride salt.
Boiling point 160 to 170 °C (320 to 338 °F; 433 to 443 K) Boiling point for freebase at 0.05mm/Hg.
log P 2.75270
Vapor pressure 7.42x10−07mm/Hg
1.614
Pharmacology
Oral, Vaporized
Pharmacokinetics:
Unknown, likely under several hours.
Several hours.
Legal status
Hazards
Flash point 200.3 °C (392.5 °F; 473.4 K)
Lethal dose or concentration (LD, LC):
6250 μg/kg (Rat)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Pharmacology

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Testing was performed on rats using this compound while characterizing various agonists of the 5-HT7 receptor. It is an agonist with a Ki value of 630.96nM.[4]

It has been found to act as a partial serotonin releasing agent.[5]

Very little other data exists about the pharmacological properties, metabolism, and toxicity of 5-MeO-pyr-T.

See also

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References

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  1. ^ Hunt, R. R.; Brimblecombe, R. W. (July 1967). "Synthesis and Biological Activity of Some Ring-Substituted Tryptamines". Journal of Medicinal Chemistry. 10 (4): 646–648. doi:10.1021/jm00316a027. PMID 4962512.
  2. ^ Mitzal, S. (1962). "N/A". Dissertationes Pharm. 14: 305.
  3. ^ Shulgin, Alexander; Shulgin, Ann (1997). TiHKAL, The Continuation (1st ed.). Berkeley, CA, USA: Transform Press. pp. 548–551. ISBN 0-9630096-9-9. Retrieved 7 April 2018.
  4. ^ Vermeulen, Erik S.; Schmidt, Anne W.; Sprouse, Jeffrey S.; Wikström, Håkan V.; Grol, Cor J. (2003). "Characterization of the 5-HT7 Receptor. Determination of the Pharmacophore for 5-HT7 Receptor Agonism and CoMFA-Based Modeling of the Agonist Binding Site". Journal of Medicinal Chemistry. 46 (25): 5365–5374. doi:10.1021/jm030826m. PMID 14640545.
  5. ^ Puigseslloses P, Nadal-Gratacós N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, Islam MN, Holy M, Niello M, Pubill D, Camarasa J, Escubedo E, Sitte HH, López-Arnau R (August 2024). "Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties". Mol Psychiatry. 29 (8): 2346–2358. doi:10.1038/s41380-024-02506-8. PMC 11412900. PMID 38486047.


 

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