4-羟基-N-甲基-N-乙基色胺

4-羟基-N-甲基-N-乙基色胺
臨床資料
其他名稱	4-OH-MET; 4-Hydroxy-N-methyl-N-ethyltryptamine; Metocin; Methylcybin
给药途径	口服
藥物類別	非选择性（英语：Binding selectivity）血清素受体激动剂; 血清素5-HT2A受体激动剂; 血清素能迷幻药; 致幻剂
ATC碼	未分配;
法律規範狀態
法律規範	美：未列入管制; 弗吉尼亚州：Schedule I Controlled substance;
藥物動力學數據
藥效起始時間（英语：Onset of action）	≤30分钟
作用時間	4–6小时
识别信息
	IUPAC命名法 32-[Ethyl(methyl)amino]ethyl1H-indol-4-ol; ;
CAS号	77872-41-4
PubChem CID	21786582;
ChemSpider	10513072;
UNII	6RN01B78NY;
CompTox Dashboard (EPA)	DTXSID70228491 ;
化学信息
化学式	C13H18N2O
摩尔质量	218.30 g·mol−1
3D模型（JSmol）	交互式图像;
	SMILES CCN(C)CCc2c[nH]c1cccc(O)c12;
	InChI InChI=1S/C13H18N2O/c1-3-15(2)8-7-10-9-14-11-5-4-6-12(16)13(10)11/h4-6,9,14,16H,3,7-8H2,1-2H3; Key:ORWQBKPSGDRPPA-UHFFFAOYSA-N;

4-羟基-N-甲基-N-乙基色胺（英語：4-hydroxy-N-methyl-N-ethyltryptamine，简称4-HO-MET），又称metocin或methylcybin，是一种属于色胺衍生物（英语：Substituted tryptamine）和4-羟色胺（英语：4-Hydroxytryptamine#Derivatives）家族的迷幻药物，是赛洛新（4-HO-DMT）的结构类似物，也是N-甲基-N-乙基色胺（英语：Methylethyltryptamine）（MET）的4-羟基类似物^[1]。该药物是口服的^[1]。

4-HO-MET是一种非选择性（英语：Binding selectivity）血清素受体激动剂，包括血清素 5-HT_2A受体^[4]^[5]^[6]^[7]。

4-HO-MET是亚历山大·舒尔金（Alexander Shulgin）在20世纪70年代发现的^[8]^[9]^[1]。1981年，David Repke（英语：David Repke）及其同事首次在文献中描述了它^[10]。从2008年开始，该药物被用作一种新型娱乐性策划药^[11]。

药效学

4-HO-MET可与多种血清素受体结合，已知其可作为血清素 5-HT_2A、5-HT_2B、5-HT2C（英语：5-HT2C）和5-HT_1A受体的激动剂^[4]^[5]^[6]^[7]。像4-HO-MET这样的血清素能致幻剂的致幻作用被认为是通过激活血清素5-HT_2A受体介导的^[12]。

参见

色胺衍生物（英语：Substituted tryptamine）
4-乙酰氧基-N-甲基-N-乙基色胺（4-AcO-MET）

参考来源

^ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 Shulgin A, Shulgin A. #21. 4-HO-MET. Isomer Design. Transform Press. 1997-09 [2023-11-28].
^ § 54.1-3446. Schedule I.. Virginia Law. [2023-10-29].
^ Kjellgren A, Soussan C. Heaven and hell--a phenomenological study of recreational use of 4-HO-MET in Sweden. J Psychoactive Drugs. 2011, 43 (3): 211–219. PMID 22111404. doi:10.1080/02791072.2011.605699.
^ ^4.0 ^4.1 Rickli A, Moning OD, Hoener MC, Liechti ME. Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens (PDF). European Neuropsychopharmacology. 2016-08, 26 (8): 1327–1337. PMID 27216487. S2CID 6685927. doi:10.1016/j.euroneuro.2016.05.001.
^ ^5.0 ^5.1 Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, Baumann MH. Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice. ACS Pharmacol Transl Sci. 2023-04, 6 (4): 567–577. PMC 10111620 . PMID 37082754. doi:10.1021/acsptsci.2c00222.
^ ^6.0 ^6.1 Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI. Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter. J Pharmacol Exp Ther. 2023-04, 385 (1): 62–75. PMC 10029822 . PMID 36669875. doi:10.1124/jpet.122.001454.
^ ^7.0 ^7.1 Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt AL. Investigation of the Structure-Activity Relationships of Psilocybin Analogues. ACS Pharmacol Transl Sci. 2021-04, 4 (2): 533–542. PMC 8033608 . PMID 33860183. doi:10.1021/acsptsci.0c00176.
^ Palamar JJ, Acosta P. A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines. Human Psychopharmacology. 2020-01, 35 (1). PMC 6995261 . PMID 31909513. doi:10.1002/hup.2719.
^ Zamberlan F, Sanz C, Martínez Vivot R, Pallavicini C, Erowid F, Erowid E, Tagliazucchi E. The Varieties of the Psychedelic Experience: A Preliminary Study of the Association Between the Reported Subjective Effects and the Binding Affinity Profiles of Substituted Phenethylamines and Tryptamines. Front Integr Neurosci. 2018, 12. PMC 6235949 . PMID 30467466. doi:10.3389/fnint.2018.00054 . 4-OH-MET (4-Hydroxy-N-methyl-N-ethyltryptamine): substituted tryptamine and close analog of psilocin, first synthesized by A. Shulgin (Shulgin and Shulgin, 1997).
^ Repke DB, Ferguson WJ, Bates DK. Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-( N -methyl- N -alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols. Journal of Heterocyclic Chemistry. 1981, 18 (1): 175–179. ISSN 0022-152X. doi:10.1002/jhet.5570180131.
^ 2015 Annual Reports on the implementation of Council Decision 2005/387/JHA. Europol. 2008 [2025-03-30].
^ Nichols DE. Psychedelics (PDF). Pharmacol Rev. 2016-04, 68 (2): 264–355. PMC 4813425 . PMID 26841800. doi:10.1124/pr.115.011478.

外部链接

[TiHKAL-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 Shulgin A, Shulgin A. #21. 4-HO-MET. Isomer Design. Transform Press. 1997-09 [2023-11-28].

[2] § 54.1-3446. Schedule I.. Virginia Law. [2023-10-29].

[KjellgrenSoussan2011-3] Kjellgren A, Soussan C. Heaven and hell--a phenomenological study of recreational use of 4-HO-MET in Sweden. J Psychoactive Drugs. 2011, 43 (3): 211–219. PMID 22111404. doi:10.1080/02791072.2011.605699.

[RickliMoningHoener2016-4] 4.0 ^4.1 Rickli A, Moning OD, Hoener MC, Liechti ME. Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens (PDF). European Neuropsychopharmacology. 2016-08, 26 (8): 1327–1337. PMID 27216487. S2CID 6685927. doi:10.1016/j.euroneuro.2016.05.001.

[GlatfelterNaeemPham2023-5] 5.0 ^5.1 Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, Baumann MH. Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice. ACS Pharmacol Transl Sci. 2023-04, 6 (4): 567–577. PMC 10111620 . PMID 37082754. doi:10.1021/acsptsci.2c00222.

[KozellEshlemanSwanson2023-6] 6.0 ^6.1 Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI. Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter. J Pharmacol Exp Ther. 2023-04, 385 (1): 62–75. PMC 10029822 . PMID 36669875. doi:10.1124/jpet.122.001454.

[KleinChathaLaskowski2021-7] 7.0 ^7.1 Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt AL. Investigation of the Structure-Activity Relationships of Psilocybin Analogues. ACS Pharmacol Transl Sci. 2021-04, 4 (2): 533–542. PMC 8033608 . PMID 33860183. doi:10.1021/acsptsci.0c00176.

[PalamarAcosta2020-8] Palamar JJ, Acosta P. A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines. Human Psychopharmacology. 2020-01, 35 (1). PMC 6995261 . PMID 31909513. doi:10.1002/hup.2719.

[ZamberlanSanzMartínez2018-9] Zamberlan F, Sanz C, Martínez Vivot R, Pallavicini C, Erowid F, Erowid E, Tagliazucchi E. The Varieties of the Psychedelic Experience: A Preliminary Study of the Association Between the Reported Subjective Effects and the Binding Affinity Profiles of Substituted Phenethylamines and Tryptamines. Front Integr Neurosci. 2018, 12. PMC 6235949 . PMID 30467466. doi:10.3389/fnint.2018.00054 . 4-OH-MET (4-Hydroxy-N-methyl-N-ethyltryptamine): substituted tryptamine and close analog of psilocin, first synthesized by A. Shulgin (Shulgin and Shulgin, 1997).

[RepkeFergusonBates1981-10] Repke DB, Ferguson WJ, Bates DK. Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-( N -methyl- N -alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols. Journal of Heterocyclic Chemistry. 1981, 18 (1): 175–179. ISSN 0022-152X. doi:10.1002/jhet.5570180131.

[Europol2008-11] 2015 Annual Reports on the implementation of Council Decision 2005/387/JHA. Europol. 2008 [2025-03-30].

[Nichols2016-12] Nichols DE. Psychedelics (PDF). Pharmacol Rev. 2016-04, 68 (2): 264–355. PMC 4813425 . PMID 26841800. doi:10.1124/pr.115.011478.

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