3-Hydroxy-N,N-dimethylphenethylamine

3-Hydroxy-N,N-dimethylphenethylamine
Clinical data
Other names	LSM-6; LSM6
Routes of; administration	Unspecified
Drug class	Adrenergic and serotonergic agent
Identifiers
	IUPAC name 3-[2-(dimethylamino)ethyl]phenol;
PubChem CID	3029884 ;
ChemSpider	2295140 ;
CompTox Dashboard (EPA)	DTXSID00901124 ;
Chemical and physical data
Formula	C10H15NO
Molar mass	165.236 g·mol−1
3D model (JSmol)	Interactive image ;
	SMILES CN(C)CCC1=CC(=CC=C1)O;
	InChI InChI=1S/C10H15NO/c1-11(2)7-6-9-4-3-5-10(12)8-9/h3-5,8,12H,6-7H2,1-2H3; Key:DZZZXJVECUJDRB-UHFFFAOYSA-N;

Last updated March 19, 2025

3-Hydroxy-N,N-dimethylphenethylamine (developmental code name LSM-6) is a drug of the phenethylamine family which was under development for the treatment of mood disorders but was never marketed.^[1]^[2] It is the N,N-dimethylated derivative of meta-tyramine (3-hydroxyphenethylamine).^[3] The drug is a naturally occurring constituent of Limacia scanden Lour. and is described as an adrenergic and serotonergic agent.^[1]^[2] It may act as a monoamine releasing agent and/or reuptake inhibitor.^[2] LSM-6 has sympathomimetic effects.^[2] It was being developed in the 1990s in Malaysia.^[1] The drug reached the preclinical research stage of development prior to its discontinuation.^[1]^[2]

References

1 2 3 4 5 "LSM 6 - AdisInsight". adisinsight.springer.com.
1 2 3 4 5 6 Hwi KK, Lay WB (September 1998). "Pharmacological, electrophysiological and toxicity studies of Limacia scanden Lour. (Menispermaceae)". J Ethnopharmacol. 62 (2): 137–148. doi:10.1016/s0378-8741(98)00045-2. PMID 9741886.
↑ "Phenol, 3-(2-dimethylamino)ethyl-". PubChem. Retrieved 1 March 2025.

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[AdisInsight-1] 1 2 3 4 5 "LSM 6 - AdisInsight". adisinsight.springer.com.

[KimKahHwiWongBeeLay1998-2] 1 2 3 4 5 6 Hwi KK, Lay WB (September 1998). "Pharmacological, electrophysiological and toxicity studies of Limacia scanden Lour. (Menispermaceae)". J Ethnopharmacol. 62 (2): 137–148. doi:10.1016/s0378-8741(98)00045-2. PMID 9741886.

[PubChem-3] "Phenol, 3-(2-dimethylamino)ethyl-". PubChem. Retrieved 1 March 2025.

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[2]

[3]

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-iBu 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-tBu 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 Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: Biscaline BOH Buscaline DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 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 ZDCM-04 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 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 Propylone
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 Venlafaxine

Clinical data

Other names	LSM-6; LSM6
Routes of administration	Unspecified^[1]
Drug class	Adrenergic and serotonergic agent ^[2]
Identifiers
IUPAC name 3-[2-(dimethylamino)ethyl]phenol
PubChem CID	3029884
ChemSpider	2295140
CompTox Dashboard (EPA)	DTXSID00901124
Chemical and physical data
Formula	C₁₀H₁₅NO
Molar mass	165.236 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN(C)CCC1=CC(=CC=C1)O
InChI InChI=1S/C10H15NO/c1-11(2)7-6-9-4-3-5-10(12)8-9/h3-5,8,12H,6-7H2,1-2H3 Key:DZZZXJVECUJDRB-UHFFFAOYSA-N

3-Hydroxy-N,N-dimethylphenethylamine

See also

References