CAS 304-21-2|Harmaline

Introduction：Basic information about CAS 304-21-2|Harmaline, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Harmaline BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles34
8. Synonyms

Common Name	Harmaline
CAS Number	304-21-2	Molecular Weight	214.263
Density	1.3±0.1 g/cm3	Boiling Point	426.4±45.0 °C at 760 mmHg
Molecular Formula	C₁₃H₁₄N₂O	Melting Point	232-234 °C(lit.)
MSDS	ChineseUSA	Flash Point	211.7±28.7 °C

Names

Name	harmaline
Synonym	More Synonyms

Harmaline BiologicalActivity

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 OxidaseResearch 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.

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
InChIKey	RERZNCLIYCABFS-UHFFFAOYSA-N
SMILES	COc1ccc2c3c([nH]c2c1)C(C)=NCC3

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

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%

Articles34

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The increasing number of new psychoactive substances (NPS) present in the illicit market render their identification in biological fluids/tissues of great concern for clinical and forensic toxicology....

Fast determination of harmala alkaloids in edible algae by capillary electrophoresis mass spectrometry.

Anal. Bioanal. Chem 407(13) , 3637-45, (2015)

The use of algae as a foodstuff is rapidly expanding worldwide from the East Asian countries, where they are also used for medical care. Harmala alkaloids (HAlk) are a family of bioactive compounds fo...

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J. Pharm. Biomed. Anal. 94 , 215-20, (2014)

Acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) are legitimate therapeutic targets for Alzheimer's disease. The classical approach for screening potential AChE/BChE inhibitors was develop...

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

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