Chemistry:N-Methylanhalinine

N-Methylanhalinine
Names
	IUPAC name 6,7,8-trimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
	Other names 1,2,3,4-Tetrahydro-6,7,8-trimethoxy-2-methylisoquinoline; O-Methylanhalidine
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	536121;
PubChem CID	616877;
	InChI InChI=1S/C13H19NO3/c1-14-6-5-9-7-11(15-2)13(17-4)12(16-3)10(9)8-14/h7H,5-6,8H2,1-4H3 Key: WMHZXZCCGOMWEQ-UHFFFAOYSA-N;
	SMILES CN1CCC2=CC(=C(C(=C2C1)OC)OC)OC;
Properties
Chemical formula	C13H19NO3
Molar mass	237.299 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

N-Methylanhalinine, also known as O-methylanhalidine, is a tetrahydroisoquinoline alkaloid found in various Turbinicarpus cactus species.^[1]^[2]^[3] It has been found to act as a potent inverse agonist of the serotonin 5-HT₇ receptor.^[4] The compound is several-fold more potent as a serotonin 5-HT₇ receptor inverse agonist than its parent compound anhalinine.^[4]

References

↑ Štarha, Roman; Chybidziurová, Adéla; Lacný, Zdenek (1999). "Alkaloids of the genus Turbinicarpus (Cactaceae)". Biochemical Systematics and Ecology 27 (8): 839–841. doi:10.1016/S0305-1978(99)00019-8. Bibcode: 1999BioSE..27..839S. https://linkinghub.elsevier.com/retrieve/pii/S0305197899000198. Retrieved 21 May 2025.
↑ Keeper Trout & friends (2013). Trout's Notes on The Cactus Alkaloids Nomenclature, Physical properties, Pharmacology & Occurrences (Sacred Cacti Fourth Edition, Part C: Cactus Chemistry: Section 1). Mydriatic Productions/Better Days Publishing. https://troutsnotes.com/pdf/C13_CactusAlkaloids.pdf.
↑ Reti, L. (1954). "Chapter 26 Simple Isoquinoline Alkaloids". The Alkaloids: Chemistry and Physiology. 4. Elsevier. p. 7–21. doi:10.1016/s1876-0813(08)60153-0. ISBN 978-0-12-469504-7. https://linkinghub.elsevier.com/retrieve/pii/S1876081308601530. Retrieved 21 May 2025.
↑ ^4.0 ^4.1 "Synthesis, Pharmacological Characterization, and Binding Mode Analysis of 8-Hydroxy-Tetrahydroisoquinolines as 5-HT7 Receptor Inverse Agonists". ACS Chem Neurosci 16 (3): 439–451. February 2025. doi:10.1021/acschemneuro.4c00667. PMID 39836645.

External links

N-Methylanhalinine - Isomer Design

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/N-Methylanhalinine. Read more

[ŠtarhaChybidziurováLacný1999-1] Štarha, Roman; Chybidziurová, Adéla; Lacný, Zdenek (1999). "Alkaloids of the genus Turbinicarpus (Cactaceae)". Biochemical Systematics and Ecology 27 (8): 839–841. doi:10.1016/S0305-1978(99)00019-8. Bibcode: 1999BioSE..27..839S. https://linkinghub.elsevier.com/retrieve/pii/S0305197899000198. Retrieved 21 May 2025.

[Trout2013-2] Keeper Trout & friends (2013). Trout's Notes on The Cactus Alkaloids Nomenclature, Physical properties, Pharmacology & Occurrences (Sacred Cacti Fourth Edition, Part C: Cactus Chemistry: Section 1). Mydriatic Productions/Better Days Publishing. https://troutsnotes.com/pdf/C13_CactusAlkaloids.pdf.

[Reti1954-3] Reti, L. (1954). "Chapter 26 Simple Isoquinoline Alkaloids". The Alkaloids: Chemistry and Physiology. 4. Elsevier. p. 7–21. doi:10.1016/s1876-0813(08)60153-0. ISBN 978-0-12-469504-7. https://linkinghub.elsevier.com/retrieve/pii/S1876081308601530. Retrieved 21 May 2025.

[ChanPottieSimon2025-4] 4.0 ^4.1 "Synthesis, Pharmacological Characterization, and Binding Mode Analysis of 8-Hydroxy-Tetrahydroisoquinolines as 5-HT7 Receptor Inverse Agonists". ACS Chem Neurosci 16 (3): 439–451. February 2025. doi:10.1021/acschemneuro.4c00667. PMID 39836645.

[1]

[2]

[3]

[4]

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-BZ 3C-E 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L -Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D -Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D -DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L -DOPA (Levodopa) L -DOPS (Droxidopa) L -Phenylalanine L -Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101

Anonymous

Search

Chemistry:N-Methylanhalinine

Namespaces

More

Page actions

See also

References

External links

Navigation

Navigation

Resources

Help

googletranslator

Navigation

Wiki tools

Wiki tools

Anonymous

Search

Chemistry:N-Methylanhalinine

See also

References

External links

Navigation

Wiki tools

Page tools

Other projects

Categories