필로카르핀

필로카르핀 · 필로카르핀및그염류 · 필로카린 · actone · Pilocarpin · (3S,4R)-3-ethyl-4-((1-Methyl-1H-iMidazol-5-yl)Methyl)dihydrofuran-2(3H)-one · Ocusert · Syncarpine

https://huagongshe.com/ko/chemical/5910

식별자 및 물리적 특성

CAS No.	54-71-7
분자식	C11H16N2O2
평균 분자량	208.26 g/mol
단동위원소 질량	208.12117776 g/mol
SMILES	CC[C@@H]1C(=O)OC[C@@H]1Cc1cncn1C
InChIKey	QCHFTSOMWOSFHM-WPRPVWTQSA-N
PubChem CID	5910
ChEMBL	CHEMBL550
ChEBI	CHEBI:8207
EC No.	202-128-4
DTXSID	DTXSID1021162
현지명	필로카르핀

화학 및 물리적 성질

XLogP	1.1
극성 표면적	44.1
수소 결합 공여자 수	0
수소 결합 수용자 수	3
회전 가능 결합 수	3
무거운 원자 수	15
형식 전하	0
복잡도	245
LogP(분배 계수)	-3.031.1
Color/Form	OIL OR CRYSTALSNEEDLES
용해도	FREELY SOL IN ETHANOLINSOL IN DIETHYL ETHER /HCL/SOL IN WATER, ALC, CHLOROFORMSPARINGLY SOL IN ETHER, BENZENEALMOST INSOL IN PETROLEUM ETHERSOL IN ETHANOL, DIETHYL ETHER2.07e+00 g/L클로로포름(소량, 초음파 처리), 메탄올(약간 용해됨)
끓는 점	260 °C @ 5 MM HG (PARTIAL CONVERSION TO ISOPILOCARPINE)bp5 260° (partial conversion to isopilocarpine)
Decomposition	ON HEATING TO DECOMP, EMITS TOXIC FUMES OF NO(X).
녹는점	195-20534 °C34°
Optical Rotation	SPECIFIC OPTICAL ROTATION: +106 DEG @ 18 °C/D (2%)
Physical Description	Solid
Stability/Shelf Life	HYGROSCOPIC. /HCL/SENSITIVE TO LIGHT.STABLE IN AIR BUT AFFECTED BY LIGHT. /NITRATE/
Dissociation Constants	PK1= 7.15PK2= 12.57 @ 20 °C
Collision Cross Section	151.18 Å² [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]139.67 Å² [M+H-H2O]+ [CCS Type: TW145.44 Å² [M+H]+ [CCS Type: TW148.74 Å² [M+Na]+ [CCS Type: TW
Other Experimental Properties	WHITE CRYSTALSSLIGHTLY BITTERMP: 195-198 °CALSO GIVEN AS 204-205 °C1 G DISSOLVES IN 0.3 ML WATER, 3 ML ALCOHOL, 366 ML CHLOROFORMINSOL IN ETHER/HCL/ODORLESS, FAINTLY BITTER CRYSTALSSOLN ACID TO LITMUSPKA1= 6.8, PKA2= 1.3 /HCL/MP: 173.5-174.0 °C DECOMPSPECIFIC OPTICAL ROTATION: +77 DEG TO +83 °FOR D (SODIUM) LINE (10%)1 G DISSOLVES IN 4 ML WATER, 75 ML ALCOHOLINSOL IN CHLOROFORM, ETHER /NITRATE/SOL ARE ACID TO LITMUS /NITRATE/WHITE POWDER OR CRYSTALS FROM ALC /NITRITE/
밀도	1.1123 (rough estimate)
굴절률	1.5000 (estimate)
pKa(산도 계수)	6.87(at 30℃)
물리적 상태	34°C Liquid
색상	Colorless to light yellow
InChI	InChI=1S/C11H16N2O2/c1-3-10-8(6-15-11(10)14)4-9-5-12-7-13(9)2/h5,7-8,10H,3-4,6H2,1-2H3/t8-,10-/m0/s1
InChIKey	QCHFTSOMWOSFHM-WPRPVWTQSA-N
SMILES	O1C[C@H](CC2N(C)C=NC=2)[C@H](CC)C1=O
LogP(분배 계수)	0.120
EPA	2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, (3S,4R)- (92-13-7)

화학적 성질

Colorless crystalline solid or an oil; melts at34°C (93.2°F); dissolves in water, alcohol,and chloroform; slightly soluble in ether andbenzene.

안전 및 규제

GHS 분류	DangerH300: Fatal if swallowed [Danger Acute toxicity, oral]H330: Fatal if inhaled [Danger Acute toxicity, inhalation]P260, P264, P270, P271, P284, P301+P316, P304+P340, P316, P320, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
규제 정보	Pilocarpine: Does not have an individual approval but may be used under an appropriate group standard
기타 안전 정보	IMAP assessments - 2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, (3S-cis)-: Human health tier I assessmentIMAP assessments - 2(3H)-Furanone, 3-ethyldihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, (3S-cis)-: Environment tier I assessment
Hazard Classes and Categories	Acute Tox. 2 (100%)Acute toxicity - category 2Acute toxicity (Oral) - Category 1Acute toxicity (Dermal) - Category 1Specific target organ toxicity - Single exposure - Category 1 (nervous system)Acute Tox. 2 *
보관 조건	KEEP WELL CLOSED & PROTECTED FROM LIGHT. /HCL/
Treatment	Overdosage should be treated with atropine titration (0. 5 mg to 1. 0 mg given subcutaneously or intravenously) and supportive measures to maintain respiration and circulation. Epinephrine (0. 3 mg to 1. 0 mg, subcutaneously or intramuscularly) may also be of value in the presence of severe cardiovascular depression or bronchoconstriction. (L1712)
Hepatotoxicity	In clinical trials of pilocarpine, serum enzyme elevations were uncommon and no more frequent than with placebo. Despite, wide scale use, there have been no published reports of acute liver injury attributable to pilocarpine.
유해 작용	As the drug acts as a cholinergic agonist, pilocarpine may propagate muscarinic side effects, particularly when used in the oral form. The muscarinic receptors are present in nearly all major organ systems, and muscarinic medications can mediate autonomic function wherever the receptors are present. Due to the receptor's role in mediating the response of the parasympathetic nervous system, stimulation of the receptors will cause "rest and digest" functions throughout the distribution of M1-M5 receptor locations: the neuronal, cardiac, musculoskeletal, pulmonary, digestive, and urinary systems.

용도

개요

Pilocarpine acts by stimulating muscarinic receptors, therefore making it similar in action to acetylcholine when systematically introduced. This compound differs from acetylcholine in that it does not react with any nicotinic receptors, but by stimulating the CNS. Its effects are blocked by atropine. It has found therapeutic use in ophthalmology as a myotic agent.

역사

It has a history of hundreds of years since pilocarpine was used to treat glaucoma .In 1933, the chemical synthesis of pilocarpine was firstly reported. However, pilocarpine couldn’t be used for treatments, because its synthetic route is so long and focuses on isopilocarpine, of which the pharmacological activities are 1/20– 1/50 of pilocarpine. In 1972, DeGraw successfully synthesized the cis-homopilopic acid employing catalytic hydrogenation of precious metals and obtained pilocarpine as the main part product. Therefore, the study on the production of pilocarpine by chemical synthesis has made new progress and has been artificially synthesized .

용도

Pilocarpine occurs in the leaves of variousspecies of pilocarpus. It is used as an antidotefor atropine poisoning and in ophthalmologyto produce contraction of the pupil.