Product Name

  • Name

    BANISTERINE MONOHYDRATE

  • EINECS 207-131-4
  • CAS No. 442-51-3
  • Article Data31
  • CAS DataBase
  • Density 1.252 g/cm3
  • Solubility Soluble in DMSO (100 mM), DMF (~1.5 mg/ml), ethanol (~1.5 mg/ml), and PBS (pH 7.2, ~0.25 mg/ml). Insoluble in water.
  • Melting Point 262-264 °C(lit.)
  • Formula C13H12N2O
  • Boiling Point 421.4 °C at 760 mmHg
  • Molecular Weight 212.251
  • Flash Point 139.7 °C
  • Transport Information UN 1544
  • Appearance Off-white solid
  • Safety 22-24/25-36/37-26-36
  • Risk Codes 25-36-20/21/22
  • Molecular Structure Molecular Structure of 442-51-3 (BANISTERINE MONOHYDRATE)
  • Hazard Symbols HarmfulXn
  • 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;
  • PSA 37.91000
  • LogP 3.03310

Synthetic route

7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride
40959-16-8

7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride

harmine
442-51-3

harmine

Conditions
ConditionsYield
With 5 mol% Pd/C; lithium carbonate In ethanol at 150℃; for 0.166667h; Sealed tube; Microwave irradiation;99%
tetrahydroharmine
486-93-1, 17019-01-1

tetrahydroharmine

harmine
442-51-3

harmine

Conditions
ConditionsYield
With sulfuric acid In 2,2,2-trifluoroethanol for 30h; Reflux;91%
With 5%-palladium/activated carbon In toluene for 24h; Reflux;72%
With water; palladium; maleic acid
7-methoxy-1-methyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

7-methoxy-1-methyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

harmine
442-51-3

harmine

Conditions
ConditionsYield
Stage #1: 7-methoxy-1-methyl-2-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole In tetrahydrofuran at -78℃; for 2h;
Stage #2: With oxygen In tetrahydrofuran at 20℃;		76%
harmaline
304-21-2

harmaline

harmine
442-51-3

harmine

Conditions
ConditionsYield
With carbon dioxide; DBN; Eosin Y In dimethyl sulfoxide at 25 - 30℃; Irradiation;71%
With hydrogenchloride; nitric acid
With sulfuric acid; permanganate(VII) ion
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

1-benzenesulfonyl-6-methoxy-3-vinyl-1H-indole
575433-20-4

1-benzenesulfonyl-6-methoxy-3-vinyl-1H-indole

harmine
442-51-3

harmine

Conditions
ConditionsYield
Stage #1: 1-benzenesulfonyl-6-methoxy-3-vinyl-1H-indole With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h;
Stage #2: N,N-dimethyl acetamide In tetrahydrofuran at -78 - -10℃;
Stage #3: With hydroxylamine hydrochloride; sodium acetate In 1,2-dichloro-benzene for 8h; Heating;		56%

Harmine Chemical Properties

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

Harmine 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.

Harmine 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

Harmine 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.

Harmine 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

Harmine 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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