암페타민

위키백과, 우리 모두의 백과사전.
둘러보기로 가기 검색하러 가기
암페타민
An image of the amphetamine compound
A 3d image of the D-amphetamine compound
체계적 명칭 (IUPAC 명명법)
(RS)-1-phenylpropan-2-amine
식별 정보
CAS 등록번호 300-62-9
ATC 코드 N06BA01
PubChem 3007
드러그뱅크 DB00182
ChemSpider 13852819
화학적 성질
화학식 C9H13N 
분자량 135.20622 g/mol[1]
SMILES eMolecules & PubChem
유의어 α-methylphenethylamine
물리적 성질
밀도 .936 g/cm³
녹는점 11.3 °C (52 °F) (predicted)[2]
끓는점 203 °C (397 °F) at 760 mmHg[3]
약동학 정보
생체적합성 Oral: 75–100%[4]
단백질 결합 15–40%[5]
약물 대사 CYP2D6,[6] DBH,[7][8] FMO3[7][9][10]
생물학적 반감기 D-amph: 9–11 hours[6][11]
L-amph: 11–14 hours[6][11]
pH-dependent: 7–34 hours[12]
배출 Primarily renal;
pH-dependent range: 1–75%[6]
처방 주의사항
임부투여안전성 C(미국)
법적 지위 통제 (S8) (오스트레일리아) Schedule I (캐나다) Class B (영국) Schedule II (미국)
중독 경향 Physical: none[13]
Psychological: moderate[14]
투여 방법 Medical: oral, intravenous[15]
Recreational: oral, insufflation, rectal, intravenous, intramuscular

암페타민(Amphetamine, alpha-methylphenethylamine의 준말)은 피로식욕을 낮추고 기민성을 증가시키는 페네틸아민 계열의 각성 중 하나이다. 주의력결핍 과다행동장애(ADHD), 기면증의 치료를 위해 승인되었다.[15] 역사적으로는 비충혈 제거제로서 의학적으로 쓰여왔으며 우울증비만증 치료 목적으로도 쓰여왔다.[15][16][17]

합성[편집]

암페타민 합성 경로
방식 1
방식 2
방식 3

약리학적 역사[편집]

약리 효과는 각성효과이다. 2차세계 대전 당시 일본에서 잠을 자지 않고 일하게 하기 위해 사용하면서 각성제로 널리 사용되었다. 습관성, 중독성이 있어 현재는 마약류와 같이 사용에 법적으로 금지된 약물이다. 흔히 말하는 잠 안 오는 약으로 사용되었다.

같이 보기[편집]

참조[편집]

  1. 〈Compound Summary〉. 《Amphetamine》. 《PubChem Compound Database》. United States National Library of Medicine – National Center for Biotechnology Information. 2015년 4월 11일. 2015년 4월 17일에 확인함. 
  2. 〈Properties: Predicted – EPISuite〉. 《Amphetamine》. 《ChemSpider》. Royal Society of Chemistry. 2013년 11월 6일에 확인함. 
  3. 〈Chemical and Physical Properties〉. 《Amphetamine》. 《PubChem Compound Database》. United States National Library of Medicine – National Center for Biotechnology Information. 2013년 10월 13일에 확인함. 
  4. 〈Pharmacology〉. 《Dextroamphetamine》. 《DrugBank》. University of Alberta. 2013년 2월 8일. 2013년 11월 5일에 확인함. 
  5. 〈Pharmacology〉. 《Amphetamine》. 《DrugBank》. University of Alberta. 2013년 2월 8일. 2013년 11월 5일에 확인함. 
  6. “Adderall XR Prescribing Information” (PDF). 《United States Food and Drug Administration》. Shire US Inc. December 2013. 12–13쪽. 2013년 12월 30일에 확인함. 
  7. Glennon RA (2013). 〈Phenylisopropylamine stimulants: amphetamine-related agents〉. Lemke TL, Williams DA, Roche VF, Zito W. 《Foye's principles of medicinal chemistry》 7판. Philadelphia, USA: Wolters Kluwer Health/Lippincott Williams & Wilkins. 646–648쪽. ISBN 9781609133450. The simplest unsubstituted phenylisopropylamine, 1-phenyl-2-aminopropane, or amphetamine, serves as a common structural template for hallucinogens and psychostimulants. Amphetamine produces central stimulant, anorectic, and sympathomimetic actions, and it is the prototype member of this class (39). ... The phase 1 metabolism of amphetamine analogs is catalyzed by two systems: cytochrome P450 and flavin monooxygenase. ... Amphetamine can also undergo aromatic hydroxylation to p-hydroxyamphetamine. ... Subsequent oxidation at the benzylic position by DA β-hydroxylase affords p-hydroxynorephedrine. Alternatively, direct oxidation of amphetamine by DA β-hydroxylase can afford norephedrine. 
  8. Taylor KB (January 1974). “Dopamine-beta-hydroxylase. Stereochemical course of the reaction” (PDF). 《J. Biol. Chem.》 249 (2): 454–458. PMID 4809526. 2014년 11월 6일에 확인함. Dopamine-β-hydroxylase catalyzed the removal of the pro-R hydrogen atom and the production of 1-norephedrine, (2S,1R)-2-amino-1-hydroxyl-1-phenylpropane, from d-amphetamine. 
  9. Krueger SK, Williams DE (June 2005). “Mammalian flavin-containing monooxygenases: structure/function, genetic polymorphisms and role in drug metabolism”. 《Pharmacol. Ther.》 106 (3): 357–387. PMC 1828602. PMID 15922018. doi:10.1016/j.pharmthera.2005.01.001. 
    Table 5: N-containing drugs and xenobiotics oxygenated by FMO
  10. Cashman JR, Xiong YN, Xu L, Janowsky A (March 1999). “N-oxygenation of amphetamine and methamphetamine by the human flavin-containing monooxygenase (form 3): role in bioactivation and detoxication”. 《J. Pharmacol. Exp. Ther.》 288 (3): 1251–1260. PMID 10027866. 
  11. “Adderall IR Prescribing Information” (PDF). 《United States Food and Drug Administration》. Teva Pharmaceuticals USA, Inc. October 2015. 1–6쪽. 2016년 5월 18일에 확인함. 
  12. 〈Metabolism/Pharmacokinetics〉. 《Amphetamine》. 《United States National Library of Medicine – Toxicology Data Network》. Hazardous Substances Data Bank. 2017년 10월 2일에 원본 문서에서 보존된 문서. 2017년 10월 2일에 확인함. Duration of effect varies depending on agent and urine pH. Excretion is enhanced in more acidic urine. Half-life is 7 to 34 hours and is, in part, dependent on urine pH (half-life is longer with alkaline urine). ... Amphetamines are distributed into most body tissues with high concentrations occurring in the brain and CSF. Amphetamine appears in the urine within about 3 hours following oral administration. ... Three days after a dose of (+ or -)-amphetamine, human subjects had excreted 91% of the (14)C in the urine 
  13. Malenka RC, Nestler EJ, Hyman SE, Holtzman DM (2015). 〈Chapter 16: Reinforcement and Addictive Disorders〉. 《Molecular Neuropharmacology: A Foundation for Clinical Neuroscience》 3판. New York: McGraw-Hill Medical. ISBN 9780071827706. Pharmacologic treatment for psychostimulant addiction is generally unsatisfactory. As previously discussed, cessation of cocaine use and the use of other psychostimulants in dependent individuals does not produce a physical withdrawal syndrome but may produce dysphoria, anhedonia, and an intense desire to reinitiate drug use. 
  14. Stahl SM (March 2017). 〈Amphetamine (D,L)〉. 《Prescriber's Guide: Stahl's Essential Psychopharmacology》 6판. Cambridge, United Kingdom: Cambridge University Press. 45–51쪽. ISBN 9781108228749. 2017년 8월 5일에 확인함. 
  15. Heal DJ, Smith SL, Gosden J, Nutt DJ (2013년 6월). “Amphetamine, past and present – a pharmacological and clinical perspective”. 《J. Psychopharmacol.》 27 (6): 479–496. PMC 3666194. PMID 23539642. doi:10.1177/0269881113482532. [This] review charts advances in pharmaceutical development from the introduction of once-daily formulations of amphetamine through to lisdexamfetamine, which is the first d-amphetamine prodrug approved for the management of ADHD in children, adolescents and adults. The unusual metabolic route for lisdexamfetamine to deliver d-amphetamine makes an important contribution to its pharmacology. How lisdexamfetamine’s distinctive pharmacokinetic/pharmacodynamic profile translates into sustained efficacy as a treatment for ADHD and its reduced potential for recreational abuse is also discussed...
    Smith, Kline and French introduced Benzedrine onto the market in 1935 as a treatment for narcolepsy (for which it is still used today), mild depression, post-encephalitic Parkinsonism and a raft of other disorders (see Bett, 1946; Guttmann and Sargent, 1937; Tidy, 1938)...
    ‘Amphetamine’, which is the generic name for Benzedrine devised by the Council on Pharmacy and Chemistry of the American Medical Association, was not adopted until many years later...
    Smith, Kline and French synthesised both isomers, and in 1937 commenced marketing of d-amphetamine, which was the more potent of the two isomers, under the trade name of Dexedrine®.
     
  16. Rasmussen N (2006년 7월). “Making the first anti-depressant: amphetamine in American medicine, 1929–1950”. 《J . Hist. Med. Allied Sci.》 61 (3): 288–323. PMID 16492800. doi:10.1093/jhmas/jrj039. SKF first packaged it as an inhaler so as to exploit the base’s volatility and, after sponsoring some trials by East Coast otolaryngological specialists, began to advertise the Benzedrine Inhaler as a decongestant in late 1933. 
  17. “Methamphetamine facts”. 《DrugPolicy.org》. 2013년 10월 19일에 확인함. Like amphetamine, methamphetamine increases activity, decreases appetite and causes a general sense of well-being. Amphetamine has been used for weight control, for athletic performance and endurance, for treating mild depression, and to help truckers complete their long hauls without falling asleep. Methamphetamine has been widely marketed to women for weight loss and to treat depression. 

외부 링크[편집]