슈도에페드린

슈도에페드린 · psi-Ephedrin · D-PSEUDOEPHEDRINE · (1S,2S)-2-(METHYLAMINO)-1-PHENYLPROPAN-1-OL · (+)-Pseudoephedrine · (1S,2S)-(+)-PSEUDOEPHEDRINE · d-Pseudoephedrine base · Besan

https://huagongshe.com/ko/chemical/7028

식별자 및 물리적 특성

CAS No.	4125-58-0
분자식	C10H15NO
평균 분자량	165.23 g/mol
단동위원소 질량	165.1153641 g/mol
SMILES	CN[C@@H](C)[C@@H](O)c1ccccc1
InChIKey	KWGRBVOPPLSCSI-WCBMZHEXSA-N
PubChem CID	7028
ChEMBL	CHEMBL1590
ChEBI	CHEBI:51209
EC No.	202-018-6
DTXSID	DTXSID0023537
현지명	슈도에페드린

화학 및 물리적 성질

XLogP	0.9
극성 표면적	32.3
수소 결합 공여자 수	2
수소 결합 수용자 수	2
회전 가능 결합 수	3
무거운 원자 수	12
형식 전하	0
복잡도	121
물질 분류	Pharmaceutical
의약품	Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive CompoundsPharmaceuticals -> Used in SwitzerlandPharmaceuticals -> Listed in ZINC15
pH	AQ SOLN (1 IN 200) 10.8
SpringerMaterials Properties	Crystal structure
LogP(분배 계수)	log Kow = 0.891.14
Color/Form	Crystals from ether
용해도	Sparingly sol in waterfreely sol in alc or etherVERY SOL IN BENZENEDMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 5 mg/ml
Human Drugs	Breast FeedingLactationMilk, HumanAdrenergic AgentsAdrenergic Alpha-AgonistsCentral Nervous System StimulantsSympathomimeticsVasoconstrictor AgentsPharmaceuticals
녹는점	118-118.7 °CFINE, WHITE TO OFF-WHITE CRYSTALS OR POWDERFAINT CHARACTERISTIC ODORMP: 182-185 °CSOLN ARE NEUTRAL TO LITMUS /HCL/119 °C118-120 °C
Optical Rotation	Specific optical rotation: +51.2 deg at 20 °C/D (in ethanol)
Physical Description	Solid
Dissociation Constants	10.3 (at 0 °C)pKa = 10.25 (conjugate acid)
끓는 점	293.09°C (rough estimate)
밀도	1.0203 (rough estimate)
증기압	0.016-0.032Pa at 20-25℃
굴절률	1.5200 (estimate)
인화점	9℃
저장 조건	-20°C
물리적 상태	수정 같은
pKa(산도 계수)	pKa 9.73(H2O,t=25±0.5,I=0.01)(Approximate)
용해도	수용성 <0.5g/L(er)
Merck	13,8007
BRN	2414132
안정성	안정적인. 타기 쉬운. 강한 산화제와 호환되지 않습니다. 빛에 노출되면 변색될 수 있습니다.
InChI	1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1
InChIKey	KWGRBVOPPLSCSI-WCBMZHEXSA-N
SMILES	CN[C@@H](C)[C@@H](O)c1ccccc1
LogP(분배 계수)	0.89 at 25℃
NIST	Pseudoephedrine, (+)-(90-82-4)
EPA	Benzenemethanol, .alpha.-[(1S)-1-(methylamino)ethyl]-, (.alpha.S)- (90-82-4)

화학적 성질

white crystals

안전 및 규제

GHS 분류	WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 156 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
규제 정보	List I Chemical: A chemical specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance. (21 eCFR 1310.02)Status: Active Update: 09-07-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/10032
기타 안전 정보	IMAP assessments - Benzenemethanol, .alpha.-[1-(methylamino)ethyl]-, [S-(R,R)]-: Human health tier I assessment
FDA 요건	The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription and over-the-counter drug products, incl pseudoephedrine sulfate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Pseudoephedrine Sulfate/The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription and over-the-counter drug products, incl pseudoephedrine hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Pseudoephedrine Hydrochloride/The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies discontinued drug products. Pseudoephedrine polistirex is included on this list.. /Pseudoephedrine Polistirex /Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: pseudoephedrine hydrochloride and pseudoephedrine sulfate are included in bronchodilator drug products. /Pseudoephedrine Hydrochloride, Pseudoephedrine Sulfate/The Combat Methamphetamine Epidemic Act of 2005 has been incorporated into the Patriot Act signed by President Bush on March 9, 2006. The act bans over-the-counter sales of cold medicines that contain the ingredient pseudoephedrine, which is commonly used to make methamphetamine. The sale of cold medicine containing pseudoephedrine is limited to behind the counter. The amount of pseudoephedrine that an individual can purchase each month is limited and individuals are required to present photo identification to purchase products containing pseudoephedrine. In addition, stores are required to keep personal information about purchasers for at least two years.

용도

개요

Pseudoephedrine is a stereoisomer of ephedrine, in the drug class of sympathomimetics. It occurs naturally in plants of the genus Ephedra. Pseudoephedrine is a mixed-acting decongestant, which activates α- and β-adrenergic receptors directly by binding to the receptor itself, and indirectly by causing norepinephrine release in synaptic nerve terminals. Pseudoephedrine is also used illicitly in the production of methamphetamine. In the United States, two recent acts of legislation – the Combat Methamphetamine Epidemic Act of 2005 and the Methamphetamine Production Prevention Act of 2008– have created stringent regulation on the sale of pseudoephedrine without a prescription. Pseudoephedrine-containing products were moved behind the counter, only to be sold by the pharmacist using their professional judgment and discretion. Limitations on the quantity of pseudoephedrine that could be purchased at one time and over a period of timewere enacted, and strict record keeping was required.

용도

Pseudoephedrine is an orally active sympathomimetic amine that is used as a nasal decongestant. It exerts its decongestant action by acting directly on a-adrenergic receptors in the respiratory tract mucosa producing vasoconstriction resulting in shrinkage of swollen nasal mucous membranes, reduction of tissue hyperemia, edema, and nasal congestion, and an increase in nasal airway patency. Drainage of sinus secretions is increased and obstructed eustachian ostia may be opened. Relaxation of bronchial smooth muscle by stimulation of b-adrenergic receptors may also occur.

일반 설명

(Sudafed, Afrinol, Drixoral) isthe (S,S) diastereoisomer of ephedrine. Whereas ephedrinehas a mixed mechanism of action, L-(+)-pseudoephedrineacts mostly by an indirect mechanism and has virtually nodirect activity. The structural basis for this difference inmechanism is the stereochemistry of the carbon atom possessingthe β-OH group. In pseudoephedrine, this carbon atompossesses the (S) configuration, the wrong stereochemistryat this center for a direct-acting effect at adrenoceptors.Although it crosses the BBB (log P=1.05, pKa=9.38),L-(+)-pseudoephedrine’s lack of direct activity affords fewerCNS effects than does ephedrine. It is a naturally occurringalkaloid from the Ephedra species. This agent is found inmany OTC nasal decongestant and cold medications.Although it is less prone to increase blood pressure thanephedrine, it should be used with caution in hypertensiveindividuals, and it should not be used in combination withMAO inhibitors.