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China
Product Name: 1-Adamantanamine hydrochloride
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Shanghai Jizhi Biochemical Technology Co., Ltd
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Product Name: 1-Adamantanamine hydrochloride
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DC Chemicals Limited
China
Product Name: Amantadine HCl
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China
Product Name: Amantadine HCl
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Dayang Chem (Hangzhou) Co., Ltd.
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Product Name: 1-Adamantanamine hydrochloride
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665-66-7

665-66-7 structure

Name: 1-Adamantanamine hydrochloride
Chemical Name: amantadine hydrochloride
CAS Number: 665-66-7
Molecular Formula: C₁₀H₁₈ClN
Molecular Weight: 187.710
Catalog: API Nervous system medication Anti-shock palsy
Create Date: 2018-02-08 08:00:00
Modify Date: 2024-01-02 12:30:00
Amantadine Hydrochloride is an antiviral and an antiparkinsonian drug.Target: Influenza VirusAmantadine is an antiviral that is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extrapyramidal reactions, and for postherpetic neuralgia. Amantadine binding of M2, based on studies of a peptide representing the M2 transmembrane segment in dodecylphosphocholine micelles. Amantadine competes with protons for binding to the deprotonated tetramer, thereby stabilizing the tetramer in a slightly altered conformation. This model accounts for the observed inhibition of proton flux by amantadine [1]. In contrast to most other described channel-blocking molecules, amantadine causes the channel gate of NMDA receptors to close more quickly. Amantadine binding inhibits current flow through NMDA receptor channels but show that its main inhibitory action at pharmaceutically relevant concentrations results from stabilization of closed states of the channel [2].

Name	amantadine hydrochloride
Synonyms	Amazolon adamantanamine hydrochloride Amantadine HCl Lysovir EINECS 211-560-2 MFCD00074723 virasol 1-aminoadamantane hydrochloride Virofral 1-Adamantanaminehydrochloride Mantadix 1-adamantamine hydrochloride Midantan 1-Adamantanamine hydrochloride Adekin Mantadan 1-adamantylamine hydrochloride exp105-1 Amantadine hydrochloride Amantadine (hydrochloride)

Description	Amantadine Hydrochloride is an antiviral and an antiparkinsonian drug.Target: Influenza VirusAmantadine is an antiviral that is used in the prophylactic or symptomatic treatment of influenza A. It is also used as an antiparkinsonian agent, to treat extrapyramidal reactions, and for postherpetic neuralgia. Amantadine binding of M2, based on studies of a peptide representing the M2 transmembrane segment in dodecylphosphocholine micelles. Amantadine competes with protons for binding to the deprotonated tetramer, thereby stabilizing the tetramer in a slightly altered conformation. This model accounts for the observed inhibition of proton flux by amantadine [1]. In contrast to most other described channel-blocking molecules, amantadine causes the channel gate of NMDA receptors to close more quickly. Amantadine binding inhibits current flow through NMDA receptor channels but show that its main inhibitory action at pharmaceutically relevant concentrations results from stabilization of closed states of the channel [2].
Related Catalog	Signaling Pathways >> Anti-infection >> Influenza Virus Research Areas >> Infection
References	[1]. Salom, D., et al., pH-dependent tetramerization and amantadine binding of the transmembrane helix of M2 from the influenza A virus. Biochemistry, 2000. 39(46): p. 14160-70. [2]. Blanpied, T.A., R.J. Clarke, and J.W. Johnson, Amantadine inhibits NMDA receptors by accelerating channel closure during channel block. J Neurosci, 2005. 25(13): p. 3312-22.

Density	1.067g/cm3
Boiling Point	225.7ºC at 760 mmHg
Melting Point	>300 °C(lit.)
Molecular Formula	C₁₀H₁₈ClN
Molecular Weight	187.710
Flash Point	96ºC
Exact Mass	187.112778
PSA	26.02000
LogP	3.41620
Index of Refraction	1.558
Water Solubility	soluble

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AU4375000

CHEMICAL NAME :: 1-Adamantanamine, hydrochloride

CAS REGISTRY NUMBER :: 665-66-7

LAST UPDATED :: 199706

DATA ITEMS CITED :: 21

MOLECULAR FORMULA :: C10-H17-N.Cl-H

MOLECULAR WEIGHT :: 187.74

WISWESSER LINE NOTATION :: L66 B6 A B- C 1B ITJ BZ &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 24 mg/kg/1D-I

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Behavioral - excitement

REFERENCE :: AEMED3 Annals of Emergency Medicine. (American College of Emergency Physicians, 1125 Executive Circle, Irving, TX 75038) Volume(issue)/page/year: 19,668,1990

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 50 mg/kg

TOXIC EFFECTS :: Behavioral - coma Cardiac - pulse rate increase, without fall in BP Cardiac - pulse rate

REFERENCE :: AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 77,388,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 13 mg/kg/5D-I

TOXIC EFFECTS :: Behavioral - euphoria Behavioral - hallucinations, distorted perceptions

REFERENCE :: AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 143,1170,1985

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 286 mg/kg

TOXIC EFFECTS :: Behavioral - hallucinations, distorted perceptions Behavioral - toxic psychosis Behavioral - excitement

REFERENCE :: AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 145,267,1988

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 800 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: 19,164,1988

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 15,642,1969

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 90 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: 19,164,1988

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 700 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 15,642,1969

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 198 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: 19,164,1988

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 290 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: 19,164,1988

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 95 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: 19,164,1988

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 37 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 15,642,1969

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 360 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 15,642,1969 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 182 mg/kg

SEX/DURATION :: female 1-91 day(s) after conception

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

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 2,607,1975

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 14 mg/kg

SEX/DURATION :: female 4-6 week(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system Reproductive - Effects on Newborn - Apgar score (human only)

REFERENCE :: REPTED Reproductive Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1987- Volume(issue)/page/year: 8,89,1994

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1100 mg/kg

SEX/DURATION :: female 5 day(s) pre-mating female 1-6 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 17,272,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 720 mg/kg

SEX/DURATION :: female 9-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Newborn - live birth index (measured after birth)

REFERENCE :: GNRIDX Gendai no Rinsho. (Tokyo, Japan) V.1-10, 1967-76(?). Volume(issue)/page/year: 4,44,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 240 mg/kg

SEX/DURATION :: female 9-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: GNRIDX Gendai no Rinsho. (Tokyo, Japan) V.1-10, 1967-76(?). Volume(issue)/page/year: 4,44,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 240 mg/kg

SEX/DURATION :: female 7-12 day(s) after conception

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

REFERENCE :: GNRIDX Gendai no Rinsho. (Tokyo, Japan) V.1-10, 1967-76(?). Volume(issue)/page/year: 3,782,1969 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3199 No. of Facilities: 56 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 1161 (estimated) No. of Female Employees: 478 (estimated)

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302
Precautionary Statements	P301 + P312 + P330
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn:Harmful
Risk Phrases	R22
Safety Phrases	S22-S36/37
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	AU4375000
HS Code	2921300090

24886-73-5

~97%

665-66-7

Literature: Hays, David S.; Fu, Gregory C. Journal of Organic Chemistry, 1998 , vol. 63, # 9 p. 2796 - 2797

57680-77-0

~82%

665-66-7

Literature: Tsutsui, Hironori; Ichikawa, Tomoko; Narasaka, Koichi Bulletin of the Chemical Society of Japan, 1999 , vol. 72, # 8 p. 1869 - 1878

880-52-4

665-66-7

Literature: Organic Letters, , vol. 11, # 2 p. 433 - 436

768-94-5

665-66-7

Literature: WO2007/96124 A1, ; Page/Page column 15-16 ;

17341-91-2

~10%

665-66-7

Literature: Huard, Kim; Lebel, Helene Chemistry - A European Journal, 2008 , vol. 14, # 20 p. 6222 - 6230

24375-06-2

24375-05-1

665-66-7

Literature: Journal of Organic Chemistry, , vol. 45, # 26 p. 5239 - 5243

Precursor 5
24886-73-5 57680-77-0 880-52-4 768-94-5
24375-06-2
DownStream 10
3717-60-0 4411-25-0 5689-59-8 22110-53-8
458529-20-9 2387-23-7 274901-16-5 702-82-9
768-94-5 13072-69-0

HS Code	2921300090
Summary	2921300090 other cyclanic, cyclenic or cyclotherpenic mono- or polyamines, and their derivatives; salts thereof。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

665-66-7	13878-11-0
80121-67-1	3717-48-4
23479-44-9	3667-91-2
41100-52-1	1329802-06-3
80789-67-9	41100-45-2
1158522-08-7	940364-43-2
134104-43-1	131615-57-1
6906-52-1	930439-75-1
2137639-47-3	1018584-77-4
1375289-11-4	849349-65-1