WIN 55,212-2

WIN 55,212-2
법적 상태
법적 상태	CA: 예정외; 다음과 같습니다UK. 클래스 B ; 다음과 같습니다US. 스케줄 I ;
식별자
	IUPAC 이름 (11R)-2-메틸-11-[(모르포린-4-일)메틸]-3-(나프탈렌-1-카르보닐)-9-옥사-1-아자트리시클로[6.3.14,12.0]도데카-2,(4),-5,7-테트라엔;
CAS 번호	131543-22-1 ;
PubChem CID	5311501;
IUPHAR/BPS	733;
켐스파이더	4470978 ;
유니	5H31GI9502;
체비	CHEBI: 73295 ;
첸블	ChEMBL188 ;
CompTox 대시보드 (EPA )	DTXSID40894849 ;
화학 및 물리 데이터
공식	C27H26N2O3
몰 질량	426.516 g/120−1
3D 모델(JSmol)	인터랙티브 이미지;
	미소 CC1=C(C2=C3N1[C@H](COC3=CC=C2)CN4CCCC4)C(=O)C5=CC6=CC=CC=C65);
	인치 InChI=1S/C27H26N2O3/c1-18-25(27)22-9-4-7-19-6-2-3-8-21(19)22-23)23-10-5-24-26(23)29(1820(17-32)16-28-13-31; 키: HQVHOQAKCMIIM-HXUWFJHSA-N;
	(이게 뭐죠?) (표준)

췌장 성상 세포.하부 프레임의 셀은 WIN 55,212-2의 액션 하에 있습니다.그들은 좀 더 "quiscent"한 표현형을 가정하는 것으로 생각된다.Michalski et al.,^[2] 2008에서.

WIN 55,212-2는 아미노알킬인돌 유도체로 설명되는 화학물질로 테트라히드로카나비놀(THC)과 같은 칸나비노이드와 비슷한 효과를 내지만 화학구조는 ^[3]^[4]^[5]전혀 다르다.

WIN 55,212-2는 신경통 ^[8]쥐 모델에서 강력한 진통제로 판명된 강력한^[7] 칸나비노이드 수용체^[6] 작용제이다.리셉터 매개 ^[9]시그널링을 통해 p42 및 p44 MAP 키나제를 활성화한다.

5μM에서 WIN 55,212-2는 CB 수용체 의존 방식으로₁ ^[10]정자의 ATP 생성을 억제한다.

WIN 55,212-2는 HU-210 및 JWH-133과 함께 인지 장애 및 신경 마커 상실을 예방할 뿐만 아니라 알츠하이머병과 관련된 아밀로이드 베타 단백질에 의한 염증을 예방할 수 있다.이 항염증 작용은 칸나비노이드 수용체에서 작용제 작용을 통해 유도되며, 이는 염증을 유발하는 미세글라이어 활성화를 방지한다.

WIN 55,212-2는 CB 칸나비노이드 수용체₁(K_i = 1.9nM)의 완전작용제이며, 해당 ^[11]수용체에 대한 THC(K_i = 41nM)보다 훨씬 높은 친화력을 가진다.WIN 55,212-2는 PPARα ^[12]및 PPARγ 핵수용체의 작용제이기도 하다.

WIN 55,212-2는 실험용 생쥐에서 자발적인 바퀴가 움직이는 것을 감소시키지만, 유전적 ^[13]배경과 성별에 따라 영향을 미친다.

미국에서는 WIN 55,212-2와 같은 3-(1-나프토일) 인돌 클래스의 모든₁ CB 수용체 작용제가 Schedule I 제어 ^[14]물질이다.WIN 55,212-2는 영국에서 ^[15]불법입니다.

참고 항목

WIN 48,098 (Pravadoline)
WIN 54,461 (6-Bromopravadoline)
WIN 55,225 (JWH-200)
WIN 56,098

레퍼런스

^ "Controlled Drugs and Substance Act - Schedule II". Justice Laws Website. Government of Canada. 18 March 2021.
^ Michalski CW, Maier M, Erkan M, Sauliunaite D, Bergmann F, Pacher P, et al. (February 2008). Gluud C (ed.). "Cannabinoids reduce markers of inflammation and fibrosis in pancreatic stellate cells". PLOS ONE. 3 (2): e1701. Bibcode:2008PLoSO...3.1701M. doi:10.1371/journal.pone.0001701. PMC 2253501. PMID 18301776.
^ Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR (1992). "Aminoalkylindole Analogs: Cannabimimetic Activity of a Class of Compounds Structurally Distinct from Δ⁹-Tetrahydrocannabinol". Journal of Pharmacology and Experimental Therapeutics. 263 (3): 1118–1126. PMID 1335057.
^ Ferraro L, Tomasini MC, Gessa GL, Bebe BW, Tanganelli S, Antonelli T (August 2001). "The cannabinoid receptor agonist WIN 55,212-2 regulates glutamate transmission in rat cerebral cortex: an in vivo and in vitro study". Cerebral Cortex. 11 (8): 728–33. doi:10.1093/cercor/11.8.728. PMID 11459762.
^ Zhang Q, Ma P, Iszard M, Cole RB, Wang W, Wang G (October 2002). "In vitro metabolism of R(+)-[2,3-dihydro-5-methyl-3-[(morpholinyl)methyl]pyrrolo [1,2,3-de]1,4-benzoxazinyl]-(1-naphthalenyl) methanone mesylate, a cannabinoid receptor agonist". Drug Metabolism and Disposition. 30 (10): 1077–86. doi:10.1124/dmd.30.10.1077. PMID 12228183.
^ Felder CC, Joyce KE, Briley EM, Mansouri J, Mackie K, Blond O, et al. (September 1995). "Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors". Molecular Pharmacology. 48 (3): 443–50. PMID 7565624.
^ Meng ID, Manning BH, Martin WJ, Fields HL (September 1998). "An analgesia circuit activated by cannabinoids". Nature. 395 (6700): 381–3. Bibcode:1998Natur.395..381M. doi:10.1038/26481. PMID 9759727. S2CID 1619608.
^ Herzberg U, Eliav E, Bennett GJ, Kopin IJ (January 1997). "The analgesic effects of R(+)-WIN 55,212-2 mesylate, a high affinity cannabinoid agonist, in a rat model of neuropathic pain". Neuroscience Letters. 221 (2–3): 157–60. doi:10.1016/S0304-3940(96)13308-5. PMID 9121688. S2CID 33643599.
^ Bouaboula M, Poinot-Chazel C, Bourrié B, Canat X, Calandra B, Rinaldi-Carmona M, et al. (December 1995). "Activation of mitogen-activated protein kinases by stimulation of the central cannabinoid receptor CB1". The Biochemical Journal. 312 ( Pt 2) (Pt 2): 637–41. doi:10.1042/bj3120637. PMC 1136308. PMID 8526880.
^ Morgan DJ, Muller CH, Murataeva NA, Davis BJ, Mackie K (April 2012). "Δ9-Tetrahydrocannabinol (Δ9-THC) attenuates mouse sperm motility and male fecundity". British Journal of Pharmacology. 165 (8): 2575–83. doi:10.1111/j.1476-5381.2011.01506.x. PMC 3423255. PMID 21615727.
^ Kuster JE, Stevenson JI, Ward SJ, D'Ambra TE, Haycock DA (March 1993). "Aminoalkylindole binding in rat cerebellum: selective displacement by natural and synthetic cannabinoids". The Journal of Pharmacology and Experimental Therapeutics. 264 (3): 1352–63. PMID 8450470.
^ O'Sullivan SE (June 2016). "An update on PPAR activation by cannabinoids". British Journal of Pharmacology. 173 (12): 1899–910. doi:10.1111/bph.13497. PMC 4882496. PMID 27077495.
^ Keeney BK, Meek TH, Middleton KM, Holness LF, Garland T (June 2012). "Sex differences in cannabinoid receptor-1 (CB1) pharmacology in mice selectively bred for high voluntary wheel-running behavior". Pharmacology, Biochemistry, and Behavior. 101 (4): 528–37. doi:10.1016/j.pbb.2012.02.017. PMID 22405775. S2CID 25174208.
^ 21 U.S.C. § 812: 통제물질의 스케줄
^ "The Misuse of Drugs Act 1971 (Amendment) Order 2013". legislation.gov.uk.

추가 정보

Patwardhan AM, Jeske NA, Price TJ, Gamper N, Akopian AN, Hargreaves KM (July 2006). "The cannabinoid WIN 55,212-2 inhibits transient receptor potential vanilloid 1 (TRPV1) and evokes peripheral antihyperalgesia via calcineurin". Proceedings of the National Academy of Sciences of the United States of America. 103 (30): 11393–8. Bibcode:2006PNAS..10311393P. doi:10.1073/pnas.0603861103. PMC 1544096. PMID 16849427.
Ramírez BG, Blázquez C, Gómez del Pulgar T, Guzmán M, de Ceballos ML (February 2005). "Prevention of Alzheimer's disease pathology by cannabinoids: neuroprotection mediated by blockade of microglial activation". The Journal of Neuroscience. 25 (8): 1904–13. doi:10.1523/JNEUROSCI.4540-04.2005. PMC 6726060. PMID 15728830.

외부 링크

"Win 55,212-2 Data Sheet". Enzo Life Sciences.

[1] "Controlled Drugs and Substance Act - Schedule II". Justice Laws Website. Government of Canada. 18 March 2021.

[PSCWIN-2] Michalski CW, Maier M, Erkan M, Sauliunaite D, Bergmann F, Pacher P, et al. (February 2008). Gluud C (ed.). "Cannabinoids reduce markers of inflammation and fibrosis in pancreatic stellate cells". PLOS ONE. 3 (2): e1701. Bibcode:2008PLoSO...3.1701M. doi:10.1371/journal.pone.0001701. PMC 2253501. PMID 18301776.

[3] Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR (1992). "Aminoalkylindole Analogs: Cannabimimetic Activity of a Class of Compounds Structurally Distinct from Δ⁹-Tetrahydrocannabinol". Journal of Pharmacology and Experimental Therapeutics. 263 (3): 1118–1126. PMID 1335057.

[4] Ferraro L, Tomasini MC, Gessa GL, Bebe BW, Tanganelli S, Antonelli T (August 2001). "The cannabinoid receptor agonist WIN 55,212-2 regulates glutamate transmission in rat cerebral cortex: an in vivo and in vitro study". Cerebral Cortex. 11 (8): 728–33. doi:10.1093/cercor/11.8.728. PMID 11459762.

[5] Zhang Q, Ma P, Iszard M, Cole RB, Wang W, Wang G (October 2002). "In vitro metabolism of R(+)-[2,3-dihydro-5-methyl-3-[(morpholinyl)methyl]pyrrolo [1,2,3-de]1,4-benzoxazinyl]-(1-naphthalenyl) methanone mesylate, a cannabinoid receptor agonist". Drug Metabolism and Disposition. 30 (10): 1077–86. doi:10.1124/dmd.30.10.1077. PMID 12228183.

[6] Felder CC, Joyce KE, Briley EM, Mansouri J, Mackie K, Blond O, et al. (September 1995). "Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors". Molecular Pharmacology. 48 (3): 443–50. PMID 7565624.

[7] Meng ID, Manning BH, Martin WJ, Fields HL (September 1998). "An analgesia circuit activated by cannabinoids". Nature. 395 (6700): 381–3. Bibcode:1998Natur.395..381M. doi:10.1038/26481. PMID 9759727. S2CID 1619608.

[8] Herzberg U, Eliav E, Bennett GJ, Kopin IJ (January 1997). "The analgesic effects of R(+)-WIN 55,212-2 mesylate, a high affinity cannabinoid agonist, in a rat model of neuropathic pain". Neuroscience Letters. 221 (2–3): 157–60. doi:10.1016/S0304-3940(96)13308-5. PMID 9121688. S2CID 33643599.

[9] Bouaboula M, Poinot-Chazel C, Bourrié B, Canat X, Calandra B, Rinaldi-Carmona M, et al. (December 1995). "Activation of mitogen-activated protein kinases by stimulation of the central cannabinoid receptor CB1". The Biochemical Journal. 312 ( Pt 2) (Pt 2): 637–41. doi:10.1042/bj3120637. PMC 1136308. PMID 8526880.

[10] Morgan DJ, Muller CH, Murataeva NA, Davis BJ, Mackie K (April 2012). "Δ9-Tetrahydrocannabinol (Δ9-THC) attenuates mouse sperm motility and male fecundity". British Journal of Pharmacology. 165 (8): 2575–83. doi:10.1111/j.1476-5381.2011.01506.x. PMC 3423255. PMID 21615727.

[11] Kuster JE, Stevenson JI, Ward SJ, D'Ambra TE, Haycock DA (March 1993). "Aminoalkylindole binding in rat cerebellum: selective displacement by natural and synthetic cannabinoids". The Journal of Pharmacology and Experimental Therapeutics. 264 (3): 1352–63. PMID 8450470.

[pmid27077495-12] O'Sullivan SE (June 2016). "An update on PPAR activation by cannabinoids". British Journal of Pharmacology. 173 (12): 1899–910. doi:10.1111/bph.13497. PMC 4882496. PMID 27077495.

[13] Keeney BK, Meek TH, Middleton KM, Holness LF, Garland T (June 2012). "Sex differences in cannabinoid receptor-1 (CB1) pharmacology in mice selectively bred for high voluntary wheel-running behavior". Pharmacology, Biochemistry, and Behavior. 101 (4): 528–37. doi:10.1016/j.pbb.2012.02.017. PMID 22405775. S2CID 25174208.

[14] 21 U.S.C. § 812: 통제물질의 스케줄

[legislation.gov.uk-15] "The Misuse of Drugs Act 1971 (Amendment) Order 2013". legislation.gov.uk.

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WIN 55,212-2

네임스페이스

더

목차

참고 항목

레퍼런스

추가 정보

외부 링크

법적 상태

법적 상태	CA: 예정외^[1] 다음과 같습니다UK. 클래스 B 다음과 같습니다US. 스케줄 I
식별자
IUPAC 이름 (11R)-2-메틸-11-[(모르포린-4-일)메틸]-3-(나프탈렌-1-카르보닐)-9-옥사-1-아자트리시클로[6.3.1^4,12.0]도데카-2,(4),-5,7-테트라엔
CAS 번호	131543-22-1^N
PubChem CID	5311501
IUPHAR/BPS	733
켐스파이더	4470978^N
유니	5H31GI9502
체비	CHEBI: 73295^N
첸블	ChEMBL188^N
CompTox 대시보드 (EPA )	DTXSID40894849
화학 및 물리 데이터
공식	C₂₇H₂₆N₂O₃
몰 질량	426.516 g/120⁻¹
3D 모델(JSmol)	인터랙티브 이미지
미소 CC1=C(C2=C3N1[C@H](COC3=CC=C2)CN4CCCC4)C(=O)C5=CC6=CC=CC=C65)
인치 InChI=1S/C27H26N2O3/c1-18-25(27)22-9-4-7-19-6-2-3-8-21(19)22-23)23-10-5-24-26(23)29(1820(17-32)16-28-13-31 키: HQVHOQAKCMIIM-HXUWFJHSA-N
^NY (이게 뭐죠?) (표준)