5-MeO-NET

5-MeO-NET
Clinical data
Other names	5-Methoxy-N-ethyltryptamine
Drug class	Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonin releasing agent
ATC code	None;
Identifiers
	IUPAC name N-ethyl-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine;
CAS Number	1019-46-1;
PubChem CID	23009084;
ChemSpider	12955759;
ChEMBL	ChEMBL57888;
CompTox Dashboard (EPA)	DTXSID801274222 ;
Chemical and physical data
Formula	C13H18N2O
Molar mass	218.300 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCNCCc1c[nH]c2c1cc(OC)cc2;
	InChI InChI=1S/C13H18N2O/c1-3-14-7-6-10-9-15-13-5-4-11(16-2)8-12(10)13/h4-5,8-9,14-15H,3,6-7H2,1-2H3; Key:UNPLGMNGAFLKSH-UHFFFAOYSA-N;

5-MeO-NET, also known as 5-methoxy-N-ethyltryptamine, is a serotonin receptor agonist and serotonin releasing agent of the tryptamine family.¹²³

Use and effects

5-MeO-NET was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved).⁴

Pharmacology

Pharmacodynamics

5-MeO-NET is a potent full agonist or near-full agonist of the serotonin 5-HT_1A, 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.¹² The drug is a relatively weak serotonin releasing agent.²

It does not produce the head-twitch response (HTR), a behavioral proxy of psychedelic effects, in rodents, suggesting that it would not be hallucinogenic in humans.¹ However, 5-MeO-NET does produce the HTR if it is coadministered with a serotonin 5-HT_1A receptor antagonist like WAY-100635, suggesting that its serotonin 5-HT_1A receptor agonism masks or blocks its own serotonin 5-HT_2A receptor-mediated HTR induction.¹

Chemistry

5-MeO-NET, chemically known as 5-methoxy-N-ethyltryptamine, is a synthetic substituted tryptamine and a N-Ethyltryptamine derivative.

Analogues

Analogues of 5-MeO-NET include N-Ethyltryptamine (NET), 4-HO-NET, 4-AcO-NET, αET, 4-HO-αET, 5-MeO-αET, 5-chloro-αMT (PAL-542), 5-fluoro-αET (PAL-545), 5-MeO-MET, 5-MeO-DMT, 5-MeO-DET, 5-MeO-MPT, 5-MeO-EPT, 5-MeO-MALT, and 5-MeO-MiPT, among others.¹

History

5-MeO-NET was first described in the scientific literature by at least 1994.³ Research on 5-MeO-NET since the early 2000s has primarily focused on its interactions with serotonin receptors and other targets, as well as behavioral effects in rodent models.¹²

References

Glatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M, et al. (December 2024). "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice". ACS Chem Neurosci. 15 (24): 4458–4477. doi:10.1021/acschemneuro.4c00513. PMID 39636099.
Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC 4194234. PMID 24800892.
Glennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, et al. (June 1994). "Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines". Journal of Medicinal Chemistry. 37 (13): 1929–1935. doi:10.1021/jm00039a004. PMID 8027974.
Alexander T. Shulgin, Ann Shulgin (1997). TiHKAL: The Continuation (1st ed.). Berkeley, CA: Transform Press. ISBN 978-0-9630096-9-2. OCLC 38503252. Retrieved 30 January 2025.

External links

5-MeO-NET - Isomer Design

[GlatfelterClarkCavalco2024-1] Glatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M, et al. (December 2024). "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice". ACS Chem Neurosci. 15 (24): 4458–4477. doi:10.1021/acschemneuro.4c00513. PMID 39636099.

[BloughLandavazoDecker2014-2] Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC 4194234. PMID 24800892.

[GlennonDukatel-Bermawy1994-3] Glennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, et al. (June 1994). "Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines". Journal of Medicinal Chemistry. 37 (13): 1929–1935. doi:10.1021/jm00039a004. PMID 8027974.

[TiHKAL1997-4] Alexander T. Shulgin, Ann Shulgin (1997). TiHKAL: The Continuation (1st ed.). Berkeley, CA: Transform Press. ISBN 978-0-9630096-9-2. OCLC 38503252. Retrieved 30 January 2025.

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