Harmaline

Names

[ CAS No. ]:
304-21-2

[ Name ]:
Harmaline

[Synonym ]:
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

Biological Activity

[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]:

Signaling Pathways >> Neuronal Signaling >> Monoamine Oxidase

Research Areas >> Neurological Disease

[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.

[Related Small Molecules]

Chemical & Physical Properties

[ 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

MSDS

Click to get detail MSDS

Toxicological Information

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

Safety Information

[ 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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%

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Related Compounds

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