Ajmalicine
Systematic (IUPAC) name
(19α)-16,17-didehydro- 19-methyloxayohimban- 16-carboxylic acid methyl ester
Clinical data
Routes of Oral
Legal status
Legal status
Identifiers
CAS Number 483-04-5 N
ATC code none
PubChem CID 251561
ChemSpider 390541 Y
ChEMBL CHEMBL123325 Y
Chemical data
Formula C 21 H 24 N 2 O 3
Molar mass 352.43 g/mol
O=C(OC)\C4=C\OC(C5CN3CCc1c(nc2ccccc12)C3CC45)C
InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16+,19-/m0/s1
Y
Key:GRTOGORTSDXSFK-XJTZBENFSA-N
Y
N Y (what is this?) (verify)
Ajmalicine , also known as δ-yohimbine or raubasine , is an antihypertensive drug used in the treatment of high blood pressure .[1] Card-Lamuran , Circolene , Cristanyl , Duxil , Duxor , Hydroxysarpon , Iskedyl , Isosarpan , Isquebral , Lamuran , Melanex , Raunatin , Saltucin Co , Salvalion , and Sarpan .[1] alkaloid found naturally in various plants such as Rauwolfia spp.Catharanthus roseus Mitragyna speciosa [1] [2] [3]
Ajmalicine is structurally related to yohimbine , rauwolscine , and other yohimban derivatives . Like corynanthine , it acts as a α1 -adrenergic receptor antagonist with preferential actions over α2 -adrenergic receptors , underlying its hypotensive rather than hypertensive effects.[1] [4]
See also [ edit ] References [ edit ]
^ a b c d Wink, Michael; Roberts, M. W. (1998). Alkaloids: biochemistry, ecology, and medicinal applications ISBN 0-306-45465-3 . ^ Kurz WG, Chatson KB, Constabel F, et al. (May 1981). "Alkaloid Production in Catharanthus roseus Cell Cultures VIII1" . Planta Medica 42 (5): 22–31. doi :10.1055/s-2007-971541 . PMID 17401876 . ^ León F, Habib E, Adkins JE, Furr EB, McCurdy CR, Cutler SJ (July 2009). "Phytochemical characterization of the leaves of Mitragyna speciosa grown in U.S.A". Natural Product Communications 4 (7): 907–10. PMID 19731590 . ^ Roquebert J, Demichel P (October 1984). "Inhibition of the alpha 1 and alpha 2-adrenoceptor-mediated pressor response in pithed rats by raubasine, tetrahydroalstonine and akuammigine". European Journal of Pharmacology 106 (1): 203–5. doi :10.1016/0014-2999(84)90698-8 . PMID 6099269 .
α1
Antagonists Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Anisodamine Arotinolol Atiprosin Atypical antipsychotics (e.g., clozapine , olanzapine , quetiapine , risperidone )Benoxathian Buflomedil Bunazosin Carvedilol Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., ergotamine , dihydroergotamine , lisuride , terguride )Etoperidone Eugenodilol Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 Labetalol mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Nefazodone Neldazosin Niaprazine Nicergoline Niguldipine Pardoprunox Pelanserin Phendioxan Phenoxybenzamine Phentolamine Piperoxan Prazosin Quinazosin Ritanserin Silodosin Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline Trazodone Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin )Tricyclic antidepressants (e.g., amitriptyline , clomipramine , doxepin , imipramine , trimipramine )Trimazosin Typical antipsychotics (e.g., chlorpromazine , fluphenazine , loxapine , thioridazine )Urapidil WB-4101 Zolertine
α2
Antagonists 1-PP Adimolol Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine , clozapine , lurasidone , paliperidone , quetiapine , risperidone , zotepine )Azapirones (e.g., buspirone , tandospirone )BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan mCPP Mianserin Mirtazapine NAN-190 Olanzapine Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine SB-269970 Setiptiline Spiroxatrine Sunepitron Tolazoline Typical antipsychotics (e.g., chlorpromazine , fluphenazine , loxapine , thioridazine )Yohimbine
β
NET
Others Antihistamines (e.g., brompheniramine , chlorphenamine , pheniramine , tripelennamine )Arylcyclohexylamines (e.g., ketamine , phencyclidine )CP-39,332 EXP-561 Fezolamine Ginkgo biloba Indeloxazine Loxapine Nefazodone Nefopam Opioids (e.g., methadone , pethidine (meperidine) , tapentadol , tramadol , levorphanol )Pridefine Tedatioxetine Teniloxazine Tofenacin Tropanes (e.g., cocaine )Ziprasidone
VMATs
