Harmane

Modify Date: 2024-01-08 10:42:42

Harmane Structure
Harmane structure
Common Name Harmane
CAS Number 486-84-0 Molecular Weight 182.221
Density 1.3±0.1 g/cm3 Boiling Point 386.9±22.0 °C at 760 mmHg
Molecular Formula C12H10N2 Melting Point 235-238 °C(lit.)
MSDS Chinese USA Flash Point 176.2±13.6 °C

 Use of Harmane


Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].

 Names

Name harman
Synonym More Synonyms

 Harmane Biological Activity

Description Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].
Related Catalog
Target

hMAO-A:0.5 μM (IC50)

MAO-B:5 μM (IC50)

α2-adrenergic receptor:18 μM (IC50)

I1-Imidazoline receptor:30 nM (IC50)

References

[1]. Louis ED, et, al. Blood harmane concentrations and dietary protein consumption in essential tremor. Neurology. 2005 Aug 9;65(3):391-6.

[2]. Musgrave IF, et, al. Harmane produces hypotension following microinjection into the RVLM: possible role of I(1)-imidazoline receptors. Br J Pharmacol. 2000 Mar;129(6):1057-9.

[3]. Glover V, et, al. β-Carbolines as selective monoamine oxidase inhibitors:In vivo implications

[4]. Umezawa K, et, al. Comutagenic effect of norharman and harman with 2-acetylaminofluorene derivatives. Proc Natl Acad Sci U S A. 1978 Feb;75(2):928-30.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 386.9±22.0 °C at 760 mmHg
Melting Point 235-238 °C(lit.)
Molecular Formula C12H10N2
Molecular Weight 182.221
Flash Point 176.2±13.6 °C
Exact Mass 182.084396
PSA 28.68000
LogP 3.26
Vapour Pressure 0.0±0.8 mmHg at 25°C
Index of Refraction 1.750

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UV0280000
CHEMICAL NAME :
9H-Pyrido(3,4-b)indole, 1-methyl-
CAS REGISTRY NUMBER :
486-84-0
BEILSTEIN REFERENCE NO. :
0143898
LAST UPDATED :
199612
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C12-H10-N2
MOLECULAR WEIGHT :
182.24
WISWESSER LINE NOTATION :
T B656 EN HMJ F

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
DNA adduct

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
100 mg/L
REFERENCE :
CALEDQ Cancer Letters (Shannon, Ireland). (Elsevier Scientific Pub. Ireland Ltd., POB 85, Limerick, Ireland) V.1- 1975- Volume(issue)/page/year: 17,249,1983

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn: Harmful;
Risk Phrases 20/21
Safety Phrases S22-S24/25
RIDADR 1544
WGK Germany 3
RTECS UV0280000
Packaging Group III
Hazard Class 6.1(b)
HS Code 2933990090

 Synthetic Route

 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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 Synonyms

1-Methyl-9H-β-carboline
2-Methyl-b-carboline
Harmane
Aribine
MFCD00004957
Harman
1-Methyl-β-carboline
1-methylbetacarboline
Aribin
1-Methyl-9H-pyrid[3,4-b]indole
EINECS 207-642-2
9H-Pyrido[3,4-b]indole, 1-methyl-
Passiflorin
Loturine
1-methyl-9H-pyrido[3,4-b]indole
1-Me-carboline
Locuturine
Locuturin
Phorbol 12,13-dibutyrate
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