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4205-91-8

4205-91-8 structure

Name: Clonidine hydrochloride
Chemical Name: Clonidine hydrochloride
CAS Number: 4205-91-8
Molecular Formula: C₉H₁₀Cl₃N₃
Molecular Weight: 266.555
Catalog: API Circulatory system medication Antihypertensive drug
Create Date: 2018-08-21 12:53:40
Modify Date: 2024-01-01 20:03:06
Clonidine hydrochloride is an agonist of α2-adrenoceptor and potent antihypertensive agent.

Name	Clonidine hydrochloride
Synonyms	(2,6-dichlorophenyl)imidazolidin-2-ylidene-amine hydrochloride ipotensium catapresan klophelin Clonidine hydrochloride Isoglaucon N-(2,6-Dichlorophenyl)imidazolidin-2-imine hydrochloride (1:1) dcai hemiton Dixarit MFCD00036705 Clonidine HCl Clonidine monohydrochloride capresin Neuclon 2,6-Dichloro-N-2-imidazolidinylidenebenzenamine Monohydrochloride 2,6-dichloro-N-imidazolidin-2-ylideneaniline hydrochloride clofelin clonidine hydrochloride salt Clonistada Tenso-Timelets EINECS 224-121-5 2-(2,6-Dichlorophenylamino)-2-imidazoline Hydrochloride 2,6-Dichloro-N-(imidazolidin-2-ylidene)aniline hydrochloride (1:1) atensina DURACLON haemiton (2,6-dichloro-phenyl)-imidazolidin-2-ylidene-amine,hydrogen chloride 2-(2,6-Dichloroanilino)-2-iMidazoline Hydrochloride Catapressan N-(2,6-Dichlorophenyl)-4,5-dihydro-1H-imidazol-2-amine hydrochloride (1:1) Catapres 1H-Imidazol-2-amine, N-(2,6-dichlorophenyl)-4,5-dihydro-, hydrochloride (1:1) Clonidine (hydrochloride)

Description	Clonidine hydrochloride is an agonist of α2-adrenoceptor and potent antihypertensive agent.
Related Catalog	Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor Research Areas >> Cardiovascular Disease
In Vitro	Clonidine (0.01, 0.1 or 1 μM) significantly induces CGRP (α and β) mRNA expression in a dose-dependent manner in endothelial cells. Clonidine treatment (1 μM) for 24 h significantly increases the NO level in endothelial cells. NO pathway modulates CGRP production induced by clonidine[2].
In Vivo	Clonidine (50 μg/kg, i.p.) induces a significant decrease in body temperature of rat lasting 3 hr, with the maximum at 1 hr after administration. An intracerebroventricular pretreatment of rats with neutral doses of phentolamine 15 min before clonidine considerably antagonizes the clonidine-induced hypothermia[1]. Clonidine (0.003-0.05 mg/kg, i.p.) potently suppresses dopamine efflux in the prefrontal cortex induced by PCP. Pretreatment with the alpha-2A receptor antagonist (BRL-44408) prevents clonidine from suppressing PCP-induced dopamine overflow in the prefrontal cortex[3]. In DMSO-pretreated SO rats, clonidine (0.6 μg i.c.) has no effect on blood pressure. However, after central adenosine A1R blockade (DPCPX) in SO rats, clonidine significantly (P < 0.05, one-way ANOVA) reduces blood pressure. In contrast, in DMSO-pretreated ABD rats, clonidine (0.6 μg i.c.) causes significant reduction in blood pressure; importantly, central A1R blockade (DPCPX pretreatment) does not influence (P > 0.05, one-way ANOVA) clonidine-evoked reduction in blood pressure in ABD rats. In DPCPX-pretreated SO rats and along with the appearance of the hypotensive response, clonidine causes a significant (P < 0.05) increase in the RVLM pERK1/2 level compared with basal or clonidine treatment in DMSO-pretreated SO rats. In vehicle (DMSO)-pretreated ABD rats, clonidine significantly (P < 0.05) enhances RVLM pERK1/2, and this response is not affected by DPCPX pretreatment[4].
Animal Admin	On the day of the experiment, the flow rate is increased to 2 μL/min approximately 2 h before beginning the collection of baseline samples. Dialysates are collected every 20 min; after 4 baseline samples are collected, animals are pretreated with an intra-peritoneal (i.p.) injection of either 0.9% saline (the vehicle), clonidine (0.0033, 0.01 or 0.05 mg/kg) or guanfacine (0.05 or 0.5 mg/kg), before receiving an injection of PCP (2.5 mg/kg, i.p.) 20 min later. In a separate study, BRL (1.0 mg/kg) is administered 20 min prior to clonidine. In addition, for some control experiments, the animals only receive one injection of saline, clonidine (0.01 or 0.05 mg/kg), guanfacine (0.5 mg/kg) or BRL (1.0 mg/kg).
References	[1]. Bugajski J, et al. The involvement of central alpha-adrenergic and histamine H2-receptors in the hypothermia induced by clonidine in the rat. Neuropharmacology. 1980 Jan;19(1):9-15. [2]. Zhang YM, et al. Clonidine induces calcitonin gene-related peptide expression via nitric oxide pathway in endothelial cells. Peptides. 2009 Sep;30(9):1746-52. [3]. Jentsch JD, et al. Clonidine and guanfacine attenuate phencyclidine-induced dopamine overflow in rat prefrontal cortex: mediating influence of the alpha-2A adrenoceptor subtype. Brain Res. 2008 Dec 30;1246:41-6. [4]. Nassar N, et al. Brainstem adenosine A1 receptor signaling masks phosphorylated extracellular signal-regulated kinase 1/2-dependent hypotensive action of clonidine in conscious normotensive rats. J Pharmacol Exp Ther. 2009 Jan;328(1):83-9.

Boiling Point	319.3ºC at760mmHg
Melting Point	312 °C
Molecular Formula	C₉H₁₀Cl₃N₃
Molecular Weight	266.555
Flash Point	146.9ºC
Exact Mass	264.994019
PSA	36.42000
LogP	3.00390
Storage condition	2-8°C
Water Solubility	H2O: 50 mg/mL, clear, colorless

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NJ2490000

CHEMICAL NAME :: 2-Imidazoline, 2-(2,6-dichloroanilino)-, monohydrochloride

CAS REGISTRY NUMBER :: 4205-91-8

LAST UPDATED :: 199504

DATA ITEMS CITED :: 28

MOLECULAR FORMULA :: C9-H9-Cl2-N3.Cl-H

MOLECULAR WEIGHT :: 266.57

WISWESSER LINE NOTATION :: T5M CN BUTJ BMR BG FG &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 180 ug/kg

TOXIC EFFECTS :: Behavioral - coma Cardiac - pulse rate Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: AJEMEN American Journal of Emergency Medicine. (WB Saunders, Philadelphia, PA) V.1- 1983- Volume(issue)/page/year: 7,343,1989

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - infant

DOSE/DURATION :: 390 ug/kg

TOXIC EFFECTS :: Behavioral - coma Cardiac - pulse rate Vascular - BP elevation not characterized in autonomic section

REFERENCE :: PEDIAU Pediatrics. (American Academy of Pediatrics, P.O. Box 1034, Evanston, IL 60204) V.1- 1948- Volume(issue)/page/year: 72,500,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 126 ug/kg/4W-I

TOXIC EFFECTS :: Gastrointestinal - other changes

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 292,174,1986

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 69 ug/kg

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Vascular - BP lowering not characterized in autonomic section Vascular - pulse pressure increase

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 2,694,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 70 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - other changes

REFERENCE :: AJDCAI American Journal of Diseases of Children. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1-80(3), 1911-50; V.100- 1960- Volume(issue)/page/year: 137,171,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 100 ug/kg

TOXIC EFFECTS :: Behavioral - irritability Cardiac - EKG changes not diagnostic of specified effects Vascular - BP lowering not characterized in autonomic section

REFERENCE :: CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 14,271,1979

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 126 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Skin and Appendages - hair

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 18,366,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 91200 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - chromodacryorrhea Behavioral - tremor Behavioral - ataxia

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 26,4843,1992

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 77 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Skin and Appendages - hair

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 18,366,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 29 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 16,1038,1966

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 135 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - ataxia Skin and Appendages - hair

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 18,366,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 9,829,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 59 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - excitement Behavioral - ataxia

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 95,966,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 17600 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 16,1038,1966

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 30 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PBPSDY Pharmacological and Biochemical Properties of Drug Substances. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.1- 1977- Volume(issue)/page/year: 1,67,1977

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 16,1038,1966

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 6 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 16,1038,1966

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PBPSDY Pharmacological and Biochemical Properties of Drug Substances. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.1- 1977- Volume(issue)/page/year: 1,67,1977

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 80 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 16,1038,1966

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 30 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 16,1038,1966

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 45 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PBPSDY Pharmacological and Biochemical Properties of Drug Substances. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.1- 1977- Volume(issue)/page/year: 1,67,1977 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9100 ug/kg/13W-I

TOXIC EFFECTS :: Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count Blood - changes in leukocyte (WBC) count

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 26,4843,1992 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6 mg/kg

SEX/DURATION :: female 30 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes

REFERENCE :: ZPPLBF Zentralblatt fuer Pharmazie, Pharmakotherapie und Laboratoriums-diagnostik. (VEB Verlag Volk und Gesundheit, Neue Gruenstr. 18, 102 Berlin, Ger. Dem. Rep.) V.109- 1970- Volume(issue)/page/year: 114,251,1975

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 5 ug/kg

SEX/DURATION :: female 1 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - other effects to embryo

REFERENCE :: ANESAV Anesthesiology. (Lippincott/Harper, Journal Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740) V.1- 1940- Volume(issue)/page/year: 67,A449,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 7500 ng/kg

SEX/DURATION :: female 16 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

REFERENCE :: AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 160,471,1989

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 5 ug/kg

SEX/DURATION :: female 1 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - other effects to embryo

REFERENCE :: ANESAV Anesthesiology. (Lippincott/Harper, Journal Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740) V.1- 1940- Volume(issue)/page/year: 67,A448,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 2080 ug/kg

SEX/DURATION :: female 8-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 31,10B,1985 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5327 No. of Facilities: 53 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 859 (estimated) No. of Female Employees: 415 (estimated)

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301-H330
Precautionary Statements	Missing Phrase - N15.00950417-P260-P304 + P340 + P310-P403 + P233
Personal Protective Equipment	Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes	T+:Verytoxic;
Risk Phrases	R25;R26
Safety Phrases	S22-S26-S28-S36/37/39-S45
RIDADR	UN 2811 6.1/PG 1
WGK Germany	3
RTECS	NJ2490000
Packaging Group	III
Hazard Class	6.1(b)
HS Code	2933290090

55150-38-4

608-31-1

4205-91-8

Literature: Boehringer Ingelheim GmbH Patent: US3931216 A1, 1976 ;

5391-39-9

608-31-1

4205-91-8

Literature: Boehringer Ingelheim GmbH Patent: US3931216 A1, 1976 ;

825-43-4

608-31-1

4205-91-8

Literature: Boehringer Ingelheim GmbH Patent: US3931216 A1, 1976 ;

120-93-4

60-80-0

103-80-0

4205-91-8

Literature: Boehringer Ingelheim GmbH Patent: US3931216 A1, 1976 ;

Precursor 7
55150-38-4 608-31-1 5391-39-9 825-43-4
120-93-4 60-80-0 103-80-0
DownStream 0

HS Code	2933290090
Summary	2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

4205-91-8	144457-28-3
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1250186-91-4	1312601-07-2
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