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Related CAS#:
304-21-2 363-11-1
6027-98-1 21236-68-0
2537-74-8 63885-08-5

304-21-2

304-21-2 structure
304-21-2 structure
  • Name: Harmaline
  • Chemical Name: harmaline
  • CAS Number: 304-21-2
  • Molecular Formula: C13H14N2O
  • Molecular Weight: 214.263
  • Catalog: Natural product Alkaloid
  • Create Date: 2018-07-14 14:48:27
  • Modify Date: 2024-01-07 10:50:17
  • Harmaline is a potent and reversible monoamine oxidase inhibitor in vivo. Harmaline is a central nervous system stimulant and can be used to induce tremor in rodents.
Name harmaline
Synonyms 3,4-Dihydroharmine
Armalin
3,4-Dihydro-7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
2H-Pyrido[3,4-b]indole, 3,4-dihydro-7-methoxy-1-methyl-
7-Methoxy-1-methyl-3,4-dihydro-2H-β-carboline
Harmine,dihydro
7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole
Harmalol methyl ether
EINECS 206-152-6
MFCD00004955
3,4-Dihydro-7-methoxy-1-methyl-β-carboline
Dihydroharmine
Harmidine
O-Methylharmalol
Description Harmaline is a potent and reversible monoamine oxidase inhibitor in vivo. Harmaline is a central nervous system stimulant and can be used to induce tremor in rodents.
Related Catalog
Target

Target: Monoamine oxidase[1]
In Vitro Harmaline inhibits monoamine oxidases, thus increasing the levels of monoamine neurotransmitters (e.g., at 7-70 μM/kg in rats)[1]. Harmaline-induced tremor in rodents is a model of essential tremor. The tremor activity is dependent on harmaline dose. The first-line clinical essential tremor treatments propranolol, primidone and gabapentin and γ-hydroxybutyrate (GHB) significantly attenuate harmaline-induced tremor. The anticonvulsants valproate and carbamazepine and the mood stabilizer lithium suppress harmaline-induced tremor. The γ-amino-butyric acid (GABA) receptor subtype A receptor agonist muscimol attenuate harmaline-induced tremor. Harmaline (30 mg/kg) induces tremor in mice through the N-methyl-D-aspartate (NMDA) receptor, both competitive and non-competitive NMDA receptor antagonists, and AMPA receptor blockade, decreased harmaline-induced tremor[2].
Animal Admin Rats[1] Wistar albino rats of 160 to 190 g, fasted for 16 hr, receive various doses of Harmaline (0-70 μM/kg) either alone or 1 hr prior to subcutaneous administration of 75 mg/kg 5-hydroxytryptophan, 10 mg/kg Ro 4-1284 or 100 mg/kg iproniazid. The animals are decapitated and the 5-hydroxytryptamine of the brain (in the experiments with 5-hydroxytryptophan also of the heart) is measured spectrophotofluorometrically[1]. Mice[2] Group-housed mice are brought to the experimental room for at least 1 h to acclimate prior to testing. Following a 20 min pretreatment with vehicle or test compounds (60 min for primidone), drug-naive mice are injected with harmaline (30 mg/kg) and placed inside the Tremor Monitor chamber for a 10 min habituation period. Following the habituation period, tremor activity of the mice is measured for 8 min[2].
References

[1]. Gey, K.F, et al. Effect of α-alkylated tryptamine derivatives on 5-hydroxytryptamine metabolism in vivo. Brit.J.Pharmacol. 19, 161-167(1962).

[2]. Paterson NE, et al. Pharmacological characterization of harmaline-induced tremor activity in mice. Eur J Pharmacol. 2009 Aug 15;616(1-3):73-80.

Density 1.3±0.1 g/cm3
Boiling Point 426.4±45.0 °C at 760 mmHg
Melting Point 232-234 °C(lit.)
Molecular Formula C13H14N2O
Molecular Weight 214.263
Flash Point 211.7±28.7 °C
Exact Mass 214.110611
PSA 37.38000
LogP 0.66
Vapour Pressure 0.0±1.0 mmHg at 25°C
Index of Refraction 1.647

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UU9800000
CHEMICAL NAME :
3H-Pyrido(3,4-b)indole, 4,9-dihydro-7-methoxy-1-methyl-
CAS REGISTRY NUMBER :
304-21-2
BEILSTEIN REFERENCE NO. :
0207310
LAST UPDATED :
199612
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C13-H14-N2-O
MOLECULAR WEIGHT :
214.29
WISWESSER LINE NOTATION :
T B656 DM HM CHJ F1 KO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
120 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
VHTODE Veterinary and Human Toxicology. (American College of Veterinary and Comparative Toxicology, Publication Office, Comparative Toxicology, Manhattan, KS 66506) V.19- 1977- Volume(issue)/page/year: 33,276,1991
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
120 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 :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
20 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 *** 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
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn
Risk Phrases R25
Safety Phrases S22-S24/25
RIDADR 1544
WGK Germany 3
RTECS UU9800000
Packaging Group III
Hazard Class 6.1(b)
HS Code 2933990090
22375-73-1 structure

22375-73-1

~%

304-21-2 structure

304-21-2
Literature: Chemische Berichte, , vol. 63, p. 120,123
106275-52-9 structure

106275-52-9

~%

304-21-2 structure

304-21-2
Literature: Canadian Journal of Chemistry, , vol. 37, p. 1851,1856
3610-36-4 structure

3610-36-4

~%

304-21-2 structure

304-21-2
Literature: Canadian Journal of Chemistry, , vol. 37, p. 1851,1856
442-51-3 structure

442-51-3

~%

304-21-2 structure

304-21-2
Literature: Chem. Zentralbl., , vol. 72, # I p. 958 Justus Liebigs Annalen der Chemie, , vol. 64, p. 365 Chemische Berichte, , vol. 18, p. 402 Chemische Berichte, , vol. 30, p. 2482
56-23-5 structure

56-23-5
22375-73-1 structure

22375-73-1

~%

304-21-2 structure

304-21-2
Literature: Chemische Berichte, , vol. 63, p. 120,123
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%

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