5-MeO-pyr-T

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	3949-14-2 ; 2426-65-5 HCl salt;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL608537 ;
ChemSpider	16153 ;
PubChem CID	17053;
UNII	L6Q3U897DF ;
CompTox Dashboard (EPA)	DTXSID50192626 ;
	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 Key: KAASYKNZNPWPQG-UHFFFAOYSA-N ; 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
Routes of; administration	Oral, Vaporized
	Pharmacokinetics:
Biological half-life	Unknown, likely under several hours.
Duration of action	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):
LDLo (lowest published)	6250 μg/kg (Rat)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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]

Pharmacology

Testing was performed on rats using this compound while characterizing various agonists of the 5-HT₇ receptor. It is an agonist with a K_i 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.

References

^ 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.
^ Mitzal, S. (1962). "N/A". Dissertationes Pharm. 14: 305.
^ 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.
^ 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.
^ 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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[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.

[PuigsesllosesNadal-GratacósKetsela2024-5] 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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5-MeO-pyr-T

Pharmacology

See also

References