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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
InChI
  • 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 Y
    Key: KAASYKNZNPWPQG-UHFFFAOYSA-N Y
  • 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
SMILES
  • O(c3ccc1c(c(c[nH]1)CCN2CCCC2)c3)C
Properties
Chemical formula
 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
Refractive index (nD)
 1.614
Pharmacology
Oral, Vaporized
Pharmacokinetics:
Unknown, likely under several hours.
Several hours.
Legal status
  • US: Unregulated Human use may be restricted under the Federal Analog Act.
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 YN ?)
Infobox references

Pharmacology

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]

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

See also

References
  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 ES, Schmidt AW, Sprouse JS, Wikström HV, Grol CJ. Characterization of the 5-HT(7) receptor. Determination of the pharmacophore for 5-HT(7) receptor agonism and CoMFA-based modeling of the agonist binding site. J Med Chem. 2003 Dec 4;46(25):5365-74. doi:10.1021/jm030826m PMID 14640545


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