Harmine

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Names

[ CAS No. ]:
442-51-3

[ Name ]:
Harmine

[Synonym ]:
9H-Pyrido(3,4-b)indole, 7-methoxy-1-methyl-
Yajeine
Banisterine
Harmine
7-Methoxy-1-methyl-9H-β-carboline
Telepathin
Yagein
Garmin
Telepathien
Harmin
Yageine
9H-Pyrido[3,4-b]indole, 7-methoxy-1-methyl-
7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
EINECS 207-131-4
Telepathine
BANISTERINE MONOHYDRATE
7-Methoxy-1-methyl-9H-pyrido(3,4-b)indole
MFCD00150055

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
421.4±40.0 °C at 760 mmHg

[ Melting Point ]:
262-264 °C(lit.)

[ Molecular Formula ]:
C₁₃H₁₂N₂O

[ Molecular Weight ]:
212.247

[ Flash Point ]:
139.8±17.0 °C

[ Exact Mass ]:
212.094955

[ PSA ]:
37.91000

[ LogP ]:
3.17

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.706

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UV0175000

CHEMICAL NAME :: 9H-Pyrido(3,4-b)indole, 7-methoxy-1-methyl-

CAS REGISTRY NUMBER :: 442-51-3

BEILSTEIN REFERENCE NO. :: 0178813

LAST UPDATED :: 199612

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C13-H12-N2-O

MOLECULAR WEIGHT :: 212.27

WISWESSER LINE NOTATION :: T B656 EN HMJ F1 KO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 3 mg/kg

TOXIC EFFECTS :: Behavioral - sleep Behavioral - tremor Gastrointestinal - nausea or vomiting

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 129,133,1928

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PSCBAY Psychopharmacology Service Center, Bulletin. (Bethesda, MD) V.1-3, 1961-65. For publisher information, see PSYBB9. Volume(issue)/page/year: 2,17,1963

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 243 mg/kg

TOXIC EFFECTS :: Behavioral - excitement Skin and Appendages - hair

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 10,1171,1976

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 129,133,1928

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 129,133,1928

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 129,133,1928

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Behavioral - excitement Behavioral - ataxia

REFERENCE :: NEPHBW Neuropharmacology. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.9- 1970- Volume(issue)/page/year: 10,15,1971

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 129,133,1928

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: QJPPAL Quarterly Journal of Pharmacy & Pharmacology. (London, UK) V.2-21, 1929-48. For publisher information, see JPPMAB. Volume(issue)/page/year: 9,37,1936 *** REVIEWS *** TOXICOLOGY REVIEW PISDDJ Pacific Information Service on Street Drugs. (J.K. Brown, School of Pharmacy, Univ. of the Pacific, Stockton, CA 95211) V.1- 1972(?)- Volume(issue)/page/year: 5(3-6),-,1977 TOXICOLOGY REVIEW CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 12,1,1978

Safety Information

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R20/21/22;R36

[ Safety Phrases ]:
S22-S24/25-S36/37-S26

[ RIDADR ]:
1544

[ WGK Germany ]:
3

[ RTECS ]:
UV0175000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

1H-Pyrido[3,4-b]indole,2,3,4,9-tetrahydro-7-methoxy-1-methyl- (9CI)
N,N-Dimethylacetamide
6-methoxy-1-(phenylsulfonyl)-3-vinyl-1H-indole
Harmaline
1-(benzenesulfonyl)-6-methoxyindole-3-carbaldehyde
6-methoxytryptamine
6-Methoxyindole
6-methoxyindole-3-acetonitrile
n-acetyl-6-methoxytryptamine
nitric acid

DownStream

Harmol
7-hydroxy-1-methyl-9H-β-carboline-6-sulfonic acid
Harmolol
9-Methoxycanthin-6-one
Harmane
9-benzyl-7-methoxy-1-methylpyrido[3,4-b]indole
Harmaline
1-methyl-9H-pyrido[3,4-b]indol-7-ol hydrobromide
1H-Pyrido[3,4-b]indole,2,3,4,9-tetrahydro-7-methoxy-1-methyl- (9CI)
1H-Pyrrolo[2,3-c]pyridine-2,3-dicarboxylicacid, 7-methyl-

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Related Compounds

Harmine-d3
Harmine.HCL
HARMINE DERIV
Harmine + tmah
Dihydroharmine
2-methylharmine
4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
(4-Methyl-tetrahydro-furan-2-yl)-methanol
N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
tert-Butyl-DL-alanine
4-amino-N-[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-ethylbenzenesulfonamide
N-[3-(Aminooxy)propyl]-N-butyl-1-butanamine