RTECS:TK6125000 The Registry of Toxic Effects of Chemical Substances

2',6' - Pipecoloxylidide, 1 - butyl - , hydrochloride, (+ - ) -

RTECS #: TK6125000

CAS #: 18010-40-7

UPDATE: November 2007 MW: 324.94 MF: C₁₈H₂₈N₂O𥺂lH

NOTE:

TOXICITY DATA HAVE NOT BEEN EVALUATED. OMISSION OF A SUBSTANCE OR NOTATION DOES NOT IMPLY ANY RELIEF FROM REGULATORY RESPONSIBILITY.

TABLE OF CONTENTS:

SYNONYMS:

ACUTE TOXICITY DATA:

OTHER MULTIPLE DOSE DATA:

REVIEWS:

REFERENCES:

SYNONYMS:

(+, - ) - 1 - Butyl - 2',6' - pipecoloxylidide monohydrochloride, monohydrate

(+ - ) - Bupivacaine hydrochloride

1 - Butyl - 2',6' - pipecoloxylidide hydrochloride (+ - )

2 - Piperidinecarboxamide, 1 - butyl - N - (2,6 - dimethylphenyl) - monohydrochloride, monohydrate

AH - 2250

Bupicaine hydrochloride (+ - )

Bupivacaine hydrochloride

LAC - 43

Marcaine hydrochloride

SKIN AND EYE IRRITATION DATA AND REFERENCES:
ROUTE/
ORGANISM DOSE
EFFECT

REFERENCE
N/R
N/R N/R N/R

MUTATION DATA AND REFERENCES:
SYSTEM TEST ROUTE/
ORGANISM/
TISSUE DOSE REFERENCE
N/R N/R N/R N/R

REPRODUCTIVE EFFECTS DATA AND REFERENCES:
ROUTE/
ORGANISM DOSE
EFFECT

REFERENCE
N/R
N/R N/R N/R

TUMORIGENIC DATA AND REFERENCES:
ROUTE/
ORGANISM DOSE
EFFECT

REFERENCE
N/R
N/R N/R N/R

ACUTE TOXICITY DATA AND REFERENCES:
ROUTE/
ORGANISM DOSE
EFFECT

REFERENCE
intramuscular
mouse lethal dose (50 percent kill): 22,753 痢/kg N/R DDREDK 21,277,1990
intraperitoneal
guinea pig lethal dose (50 percent kill): 50 mg/kg N/R NIIRDN 6,680,1982
intraperitoneal
mouse lethal dose (50 percent kill): 58,700 痢/kg Behavioral: Anticonvulsant

Behavioral: Somnolence (general depressed activity) AACRAT 60,385,1981
intratracheal
rabbit lethal dose (50 percent kill): 11 mg/kg N/R AIPTAK 200,359,1972
intravenous
domestic animal lowest published lethal dose: 150 mg/kg Cardiac: EKG changes not diagnostic of above

Behavioral: Convulsions or effect on seizure threshold AACRAT 86,797,1998
intravenous
mouse lethal dose (50 percent kill): 6,100 痢/kg N/R ANPRBG 36,79,1989
intravenous
rat lethal dose (50 percent kill): 6 mg/kg N/R AIPTAK 200,359,1972
intravenous
rabbit lethal dose (50 percent kill): 3,400 痢/kg N/R AIPTAK 200,359,1972
oral
rabbit lethal dose (50 percent kill): 18 mg/kg N/R AIPTAK 200,359,1972
parenteral
child lowest published toxic dose: 1.25 mg/kg Peripheral Nerve and Sensation: Flaccid paralysis without anesthesia (usually neuromuscular blockage)

Lung, Thorax, or Respiration: Respiratory obstruction

Lung, Thorax, or Respiration: Respiratory depression AANEAB 45,1042,2001
parenteral
rat lethal dose (50 percent kill): 30 mg/kg N/R ANESAV 89,1199,1998
parenteral
rabbit lethal dose (50 percent kill): 48 mg/kg N/R AIPTAK 200,359,1972
subcutaneous
cattle lowest published toxic dose: 19 痢/kg Peripheral Nerve and Sensation: Local anesthetic JVPTD9 24,89,2001
subcutaneous
mouse lethal dose (50 percent kill): 59 mg/kg N/R AIPTAK 200,359,1972
subcutaneous
rat lethal dose (50 percent kill): 43 mg/kg N/R AIPTAK 200,359,1972
subcutaneous
rat lowest published toxic dose: 1.59 mg/kg Behavioral: Analgesia EJPHAZ 552,67,2006

OTHER MULTIPLE DOSE DATA AND REFERENCES:
ROUTE/
ORGANISM DOSE
EFFECT

REFERENCE
subcutaneous
rat lowest published toxic dose: 560 mg/kg/4 week- intermittent Liver: Other changes

Endocrine: Other changes

Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field YAKUD5 11,2035,1969
subcutaneous
rat lowest published toxic dose: 1,680 mg/kg/12 week- intermittent Liver: Other changes

Lung, Thorax, or Respiration: Other changes

Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field YAKUD5 11,2035,1969

REVIEWS:
ORGANIZATION STANDARD
REFERENCE

TOXICOLOGY REVIEW
ENTOX* -,125,2005

STANDARDS AND REGULATIONS:
ORGANIZATION STANDARD
REFERENCE

N/R N/R N/R

NIOSH DOCUMENTATION AND SURVEILLANCE:
ORGANIZATION STANDARD or SURVEY
REFERENCE

N/R N/R N/R

STATUS IN FEDERAL AGENCIES:
ORGANIZATION
REFERENCE

N/R

REFERENCES:
CODEN
REFERENCE

AACRAT Anesthesia and Analgesia (New York). (Elsevier Science Pub. Co., Inc., 52 Vanderbilt Ave., New York, NY 10017) V.36- 1957-
AANEAB Acta Anaesthesiologica Scandinavica. (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) V.1- 1957-
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898-
ANESAV Anesthesiology. (Lippincott/Harper, Journal Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740) V.1- 1940-
ANPRBG Anesthesia Progress. (Elsevier Science Publishing Co.,Inc., 655 Avenue of the Americas, New York, NY 10010) V.13- 1966-
DDREDK Drug Development Research. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1981-
EJPHAZ European Journal of Pharmacology. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1967-
ENTOX* Encyclopedia of Toxicology: Reference Book, Elsevier, 2005
JVPTD9 Journal of Veterinary Pharmacology and Therapeutics. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1978-
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan)
YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959-

Used as a local anesthetic

FDA-proprietary drug

RTECS Compound Description:
Drug
Human Data

ALT CAS #: 14252-80-3
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SYNONYMS:
(+, - ) - 1 - Butyl - 2',6' - pipecoloxylidide monohydrochloride, monohydrate (+ - ) - Bupivacaine hydrochloride 1 - Butyl - 2',6' - pipecoloxylidide hydrochloride (+ - ) 2 - Piperidinecarboxamide, 1 - butyl - N - (2,6 - dimethylphenyl) - monohydrochloride, monohydrate AH - 2250	Bupicaine hydrochloride (+ - ) Bupivacaine hydrochloride LAC - 43 Marcaine hydrochloride

SKIN AND EYE IRRITATION DATA AND REFERENCES:
ROUTE/ ORGANISM	DOSE	EFFECT	REFERENCE
N/R	N/R	N/R	N/R

MUTATION DATA AND REFERENCES:
SYSTEM TEST	ROUTE/ ORGANISM/ TISSUE	DOSE	REFERENCE
N/R	N/R	N/R	N/R

REPRODUCTIVE EFFECTS DATA AND REFERENCES:
ROUTE/ ORGANISM	DOSE	EFFECT	REFERENCE
N/R	N/R	N/R	N/R

TUMORIGENIC DATA AND REFERENCES:
ROUTE/ ORGANISM	DOSE	EFFECT	REFERENCE
N/R	N/R	N/R	N/R

ACUTE TOXICITY DATA AND REFERENCES:
ROUTE/ ORGANISM	DOSE	EFFECT	REFERENCE
intramuscular mouse	lethal dose (50 percent kill): 22,753 痢/kg	N/R	DDREDK 21,277,1990
intraperitoneal guinea pig	lethal dose (50 percent kill): 50 mg/kg	N/R	NIIRDN 6,680,1982
intraperitoneal mouse	lethal dose (50 percent kill): 58,700 痢/kg	Behavioral: Anticonvulsant Behavioral: Somnolence (general depressed activity)	AACRAT 60,385,1981
intratracheal rabbit	lethal dose (50 percent kill): 11 mg/kg	N/R	AIPTAK 200,359,1972
intravenous domestic animal	lowest published lethal dose: 150 mg/kg	Cardiac: EKG changes not diagnostic of above Behavioral: Convulsions or effect on seizure threshold	AACRAT 86,797,1998
intravenous mouse	lethal dose (50 percent kill): 6,100 痢/kg	N/R	ANPRBG 36,79,1989
intravenous rat	lethal dose (50 percent kill): 6 mg/kg	N/R	AIPTAK 200,359,1972
intravenous rabbit	lethal dose (50 percent kill): 3,400 痢/kg	N/R	AIPTAK 200,359,1972
oral rabbit	lethal dose (50 percent kill): 18 mg/kg	N/R	AIPTAK 200,359,1972
parenteral child	lowest published toxic dose: 1.25 mg/kg	Peripheral Nerve and Sensation: Flaccid paralysis without anesthesia (usually neuromuscular blockage) Lung, Thorax, or Respiration: Respiratory obstruction Lung, Thorax, or Respiration: Respiratory depression	AANEAB 45,1042,2001
parenteral rat	lethal dose (50 percent kill): 30 mg/kg	N/R	ANESAV 89,1199,1998
parenteral rabbit	lethal dose (50 percent kill): 48 mg/kg	N/R	AIPTAK 200,359,1972
subcutaneous cattle	lowest published toxic dose: 19 痢/kg	Peripheral Nerve and Sensation: Local anesthetic	JVPTD9 24,89,2001
subcutaneous mouse	lethal dose (50 percent kill): 59 mg/kg	N/R	AIPTAK 200,359,1972
subcutaneous rat	lethal dose (50 percent kill): 43 mg/kg	N/R	AIPTAK 200,359,1972
subcutaneous rat	lowest published toxic dose: 1.59 mg/kg	Behavioral: Analgesia	EJPHAZ 552,67,2006

OTHER MULTIPLE DOSE DATA AND REFERENCES:
ROUTE/ ORGANISM	DOSE	EFFECT	REFERENCE
subcutaneous rat	lowest published toxic dose: 560 mg/kg/4 week- intermittent	Liver: Other changes Endocrine: Other changes Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field	YAKUD5 11,2035,1969
subcutaneous rat	lowest published toxic dose: 1,680 mg/kg/12 week- intermittent	Liver: Other changes Lung, Thorax, or Respiration: Other changes Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field	YAKUD5 11,2035,1969

REVIEWS:
ORGANIZATION	STANDARD	REFERENCE
TOXICOLOGY REVIEW		ENTOX* -,125,2005

STANDARDS AND REGULATIONS:
ORGANIZATION	STANDARD	REFERENCE
N/R	N/R	N/R

NIOSH DOCUMENTATION AND SURVEILLANCE:
ORGANIZATION	STANDARD or SURVEY	REFERENCE
N/R	N/R	N/R

REFERENCES:
CODEN	REFERENCE
AACRAT	Anesthesia and Analgesia (New York). (Elsevier Science Pub. Co., Inc., 52 Vanderbilt Ave., New York, NY 10017) V.36- 1957-
AANEAB	Acta Anaesthesiologica Scandinavica. (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) V.1- 1957-
AIPTAK	Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898-
ANESAV	Anesthesiology. (Lippincott/Harper, Journal Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740) V.1- 1940-
ANPRBG	Anesthesia Progress. (Elsevier Science Publishing Co.,Inc., 655 Avenue of the Americas, New York, NY 10010) V.13- 1966-
DDREDK	Drug Development Research. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1981-
EJPHAZ	European Journal of Pharmacology. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1967-
ENTOX*	Encyclopedia of Toxicology: Reference Book, Elsevier, 2005
JVPTD9	Journal of Veterinary Pharmacology and Therapeutics. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1978-
NIIRDN	Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan)
YAKUD5	Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959-