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665-66-7 13878-11-0
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665-66-7

665-66-7 structure
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
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
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 structure

24886-73-5

~97%

665-66-7 structure

665-66-7
Literature: Hays, David S.; Fu, Gregory C. Journal of Organic Chemistry, 1998 , vol. 63, # 9 p. 2796 - 2797
57680-77-0 structure

57680-77-0

~82%

665-66-7 structure

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 structure

880-52-4

~%

665-66-7 structure

665-66-7
Literature: Organic Letters, , vol. 11, # 2 p. 433 - 436
768-94-5 structure

768-94-5

~%

665-66-7 structure

665-66-7
Literature: WO2007/96124 A1, ; Page/Page column 15-16 ;
17341-91-2 structure

17341-91-2

~10%

665-66-7 structure

665-66-7
Literature: Huard, Kim; Lebel, Helene Chemistry - A European Journal, 2008 , vol. 14, # 20 p. 6222 - 6230
24375-06-2 structure

24375-06-2

~%

24375-05-1 structure

24375-05-1
665-66-7 structure

665-66-7
Literature: Journal of Organic Chemistry, , vol. 45, # 26 p. 5239 - 5243
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%

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