rugulovasine

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| ImageFile = Rugulovasine A and B.svg

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• A: (4S,5R)-4'-methyl-4-(methylamino)-3,4-dihydro-1H,5'H-spiro[benzo[cd]indole-5,2'-furan]-5'-one
• B: (4R,5R)-4'-methyl-4-(methylamino)-3,4-dihydro-1H,5'H-spiro[benzo[cd]indole-5,2'-furan]-5'-one

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| Section1 = {{Chembox Identifiers

| index_label=A

| index1_label=B

| CASNo = 26909-33-1

| CASNo2 = 26909-34-2

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| ChemSpiderID = 103037

| ChemSpiderID1 = 106408

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| PubChem = 115153

| PubChem1 = 119088

| InChI = InChI=1/C16H16N2O2/c1-9-7-16(20-15(9)19)11-4-3-5-12-14(11)10(8-18-12)6-13(16)17-2/h3-5,7-8,13,17-18H,6H2,1-2H3/t13-,16+/s2

| InChIKey = QTWQJTORJVFWAQ-WKTCHCBJNA-N

| SMILES = O=C1OC2(C=C1C)C=3C=CC=C4NC=C(C43)CC2NC

| InChI1= InChI=1/C16H16N2O2/c1-9-7-16(20-15(9)19)11-4-3-5-12-14(11)10(8-18-12)6-13(16)17-2/h3-5,7-8,13,17-18H,6H2,1-2H3/t13-,16-/s2

| InChIKey1 = QTWQJTORJVFWAQ-AYSIPDSENA-N

| SMILES1 = O=C1OC2(C=C1C)C=3C=CC=C4NC=C(C43)CC2NC

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| Section2 = {{Chembox Properties

| C=16| H=16 | N=2 | O=2

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| Section3 = {{Chembox Hazards

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Rugulovasines are bio-active alkaloids made by Penicillium.{{cite journal |last1=Dorner |first1=JW |last2=Cole |first2=RJ |last3=Hill |first3=R |last4=Wicklow |first4=D |last5=Cox |first5=RH |title=Penicillium rubrum and Penicillium biforme, new sources of rugulovasines A and B. |journal=Applied and Environmental Microbiology |date=September 1980 |volume=40 |issue=3 |pages=685–7 |doi=10.1128/aem.40.3.685-687.1980 |pmid=7425621|pmc=291639 |bibcode=1980ApEnM..40..685D }} Rugulovasine A and B bind strongly to the 5-HT_1A, 5-HT_2A, and 5-HT_2C receptors, but lack meaningful binding affinity towards the α₁ adrenergic and dopamine receptors.{{cite journal |last1=Bartoccini |first1=Francesca |last2=Regni |first2=Alessio |last3=Retini |first3=Michele |last4=Piersanti |first4=Giovanni |title=Asymmetric Total Synthesis of All Rugulovasine Stereoisomers and Preliminary Evaluation of Their Biological Properties |journal=European Journal of Organic Chemistry |date=6 May 2022 |volume=2022 |issue=17 |doi=10.1002/ejoc.202200315 |s2cid=248080578 |language=en |issn=1434-193X|doi-access=free |hdl=11576/2701930 |hdl-access=free }} Little is known about the in vivo activity of Rugulovasine A and B, although they have hypotensive effects in cats.{{cite journal |last1=Nagaoka |first1=A |last2=Kikuchi |first2=K |title=Pharmacological studies of new indole alkaloids, rugulovasine A and B hydrochloride. II. Hypotensive mechanism of both alkaloids in the anesthetized cats. |journal=Arzneimittel-Forschung |date=January 1972 |volume=22 |issue=1 |pages=143–6 |pmid=5066989}}