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Basic information

  • Name:
  • 9H-Pyrido[3,4-b]indole,7-methoxy-1-methyl-

  • Superlist Name:
  • Harmine
  • CAS No.:
  • 442-51-3

  • Formula:
  • C13H12N2O
  • Synonyms:
  • 1-Methyl-7-methoxy-b-carboline;7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole;Banisterin;Banisterine;Harmin;Leucoharmine;Telepathin;Telepathine;Yagein;Yageine;
Supplier Location:
China (Mainland)(12)United States(1)
Business Type:
Importer/Exporter(9)Lab/Research institutions(2)
Certificates:
ISO(1)Production License(0)

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Chemistry

IUPAC Name: 7-Methoxy-1-methyl-9H-pyrido[3,4-B]indole
The MF of Banisterine monohydrate (CAS NO.442-51-3) is C12H13ClN2O.

                           
The MW of Banisterine monohydrate (CAS NO.442-51-3) is 236.7.
Synonyms of Banisterine monohydrate (CAS NO.442-51-3): 1-Methyl-7-methoxy-beta-carboline ; 4-B)Indole,7-methoxy-1-methyl-9h-pyrido( ; 7-Methoxy-1-methyl-9H-beta-carboline ; Harmin ; Leucoharmine ; Telepathien ; 9H-Pyrido[3,4-b]indole, 7-methoxy-1-methyl- ; Garmin
Product Categories: Heterocyclic Compounds;Alkaloids;Biochemistry;Indole Alkaloids
Apperance: Off-White Solid
Index of Refraction: 1.706 
EINECS: 207-131-4
Density: 1.252 g/ml 
Flash Point: 139.7 °C
Boiling Point: 421.4 °C
Melting Point: 262-266 °C
Merck: 14,4616
BRN: 178813

Uses

  Banisterine monohydrate (CAS NO.442-51-3) is a CNS stimulant isolated from seeds of Peganum harmala L. Zygophyllaceae.As an MAO inhibitor, harmine inhibits the breakdown of monoamines by enzymes called monoamine oxidases.Harmine is also a useful fluorescent pH indicator. As the pH of its local environment increases, the fluorescence emission of harmine decreases.

Production

Raw materials: Acetic acid glacial-->N,N-Dimethylformamide-->Phosphorus oxychloride-->Potassium hydroxide -->Ammonia-->Azabenzene-->1-Oxa-4-azacyclohexane-->Sodium sulfide-->Potassium dichromate-->Acetaldehyde-->Aluminium-nickel-->6-Methoxyindole-->Hydantoin

Toxicity Data With Reference

1.    

ims-man TDLo:3 mg/kg:CNS,GIT

    AEPPAE    Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 129 (1928),133.
2.    

scu-mus LD50:243 mg/kg

    PCJOAU    Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. 10 (1976),1171.
3.    

ivn-mus LDLo:50 mg/kg

    AEPPAE    Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 129 (1928),133.
4.    

ivn-rat LDLo:10 mg/kg

    AEPPAE    Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 129 (1928),133.
5.    

scu-rbt LDLo:200 mg/kg

    AEPPAE    Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 129 (1928),133.
6.    

ivn-rbt LDLo:60 mg/kg

    NEPHBW    Neuropharmacology. 10 (1971),15.
7.    

scu-gpg LDLo:100 mg/kg

    AEPPAE    Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 129 (1928),133.
8.    

scu-frg LDLo:300 mg/kg

    QJPPAL    Quarterly Journal of Pharmacy and Pharmacology. 9 (1936),37.

Safety Profile

Poison by intravenous and subcutaneous routes. Human systemic effects by intramuscular route: sleep disturbance, tremors, nausea. When heated to decomposition it emits toxic fumes of NOx.Safety information of Banisterine monohydrate (CAS NO.442-51-3):
Hazard Codes  HarmfulXn
Risk Statements 
25 Toxic if swallowed
36 Irritating to the eyes
20/21/22 Harmful by inhalation, in contact with skin and if swallowed
Safety Statements 
22 Do not breathe dust
24/25 Avoid contact with skin and eyes
36/37 Wear suitable protective clothing and gloves
26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RIDADR  1544
WGK Germany  3
RTECS  UV0175000
HazardClass  6.1
PackingGroup  III

Specification

 Harmine is a fluorescent harmala alkaloid belonging to the beta-carboline family of compounds. It occurs in a number of different plants, most notably the Middle Eastern plant harmal or Syrian rue (Peganum harmala) and the South American vine Banisteriopsis caapi ('yage', 'ayahuasca'). Harmine is a reversible monoamine oxidase inhibitor (MAO inhibitor or MAOI) and CNS stimulant. It inhibits MAO-A but has no effect on MAO-B.

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