485-91-6

Basic information

• Product Name: ALLOCRYPTOPINE
• Synonyms: 3,4-DIMETHOXY-6-METHYL-5,7,8,15-TETRAHYDRO-6H-BENZO[C][1,3]DIOXOLO[4',5':4,5]BENZO[1,2-G]AZECIN-14-ONE;ALLOCRYPTOPINE;ALLOCRYPTOPINE, ALPHA-;ALPHA-ALLOCRYPTOPINE;5,7,8,15-tetrahydro-3,4-dimethoxy-6-methyl[1,3]benzodioxolo[5,6-e][2]benzazecin-14(6H)-one;5,7,8,15-Tetrahydro-3,4-dimethoxy-6-methylbenzo[e][1,3]dioxolo[4,5-k][3]benzazecin-14(6H)-one;Thalictrimine;C02134
• CAS NO: 485-91-6
• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.41
• EINECS: 207-626-5
• Product Categories: Alkaloids
• Mol File: 485-91-6.mol

Chemical Properties

• Melting Point: 160～161℃
• Boiling Point: 552.7°Cat760mmHg
• Flash Point: 288.1°C
• Appearance: /
• Density: 1.216g/cm³
• Vapor Pressure: 2.92E-12mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• PKA: 7.86±0.20(Predicted)
• CAS DataBase Reference: ALLOCRYPTOPINE(CAS DataBase Reference)
• NIST Chemistry Reference: ALLOCRYPTOPINE(485-91-6)
• EPA Substance Registry System: ALLOCRYPTOPINE(485-91-6)

Safety Data

• Hazardous Substances Data: 485-91-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ALLOCRYPTOPINE is used as a therapeutic agent for its antiparasitic, antiarrhythmic, antithrombotic, and anti-inflammatory properties. Its diverse pharmacological activities make it a valuable compound for the development of new drugs to treat various medical conditions.
Used in Antiparasitic Applications:
ALLOCRYPTOPINE is used as an antiparasitic agent to combat parasitic infections. Its effectiveness against parasites can be beneficial in treating and preventing various parasitic diseases.
Used in Cardiac Applications:
As an antiarrhythmic agent, ALLOCRYPTOPINE is used to regulate and stabilize heart rhythms, helping to prevent and treat abnormal heart beats and related cardiovascular conditions.
Used in Anticoagulant Applications:
ALLOCRYPTOPINE is used as an antithrombotic agent to prevent blood clot formation, which can be crucial in managing and treating conditions such as deep vein thrombosis, stroke, and myocardial infarction.
Used in Anti-inflammatory Applications:
ALLOCRYPTOPINE is used as an anti-inflammatory agent to reduce inflammation and alleviate pain associated with various conditions, such as arthritis, tendonitis, and other inflammatory disorders.

References

Kuchkova, Lazur'evskii., Izv. Akad. Nauk. Mold. SSR, Ser. Khim. Bioi., II, 43 (196S)

InChI:InChI=1/C21H23NO5/c1-22-7-6-14-9-19-20(27-12-26-19)10-15(14)17(23)8-13-4-5-18(24-2)21(25-3)16(13)11-22/h4-5,9-10H,6-8,11-12H2,1-3H3

Synthetic route

dihydroallocryptopine (14358-63-5, 93527-26-5) → allocryptopine (485-91-6)

Conditions	Yield
With sodium acetate; pyridinium chlorochromate In dichloromethane at 20℃; for 2h;	63%
With sodium acetate; pyridinium chlorochromate In dichloromethane for 2h;

canadine (522-97-4, 2086-96-6, 5096-57-1, 29074-38-2) → 12,13-dihydrochelerythrine (6880-91-7) + berberine iodide (4263-84-7) + allocryptopine (485-91-6)

Conditions	Yield
In water at 24℃; for 144h; incorporation experiment on Macleaya cordata in Murashige and Skoog's medium;	A 0.4% B 12.1% C 1.7%

(+/-)-cis-N-methyl-7,8,13,13a-tetrahydroberberinium chloride (16211-68-0, 24031-76-3, 37791-14-3, 57089-29-9, 59895-76-0, 85888-53-5, 85888-54-6) → 12,13-dihydrochelerythrine (6880-91-7) + allocryptopine (485-91-6)

Conditions	Yield
In water at 24℃; for 192h; incorporation experiment on Macleaya cordata in Murashige and Skoog's medium;	A 1.4% B 6.2%

diazomethane (186581-53-3, 908094-01-9) + 9-demethylallocryptopine (22047-92-3) → allocryptopine (485-91-6)

Conditions	Yield
In diethyl ether

(14Z)-3,4-dimethoxy-6-methyl-5,6,7,8-tetrahydro-benzo[c][1,3]dioxolo[4',5':4,5]benzo[1,2-g]azecine 6-oxide (41759-48-2) → allocryptopine (485-91-6)

Conditions	Yield
With hydrogenchloride In acetic acid

9,10,13a-trimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (100176-55-4) + methyl iodide (74-88-4) → allocryptopine (485-91-6)

Conditions	Yield
In methanol

(S)-N-methylcanadine (47474-49-7) → allocryptopine (485-91-6)

Conditions	Yield
With oxygen; NADPH at 30℃; for 0.333333h; tricine buffer, pH 8.5; Yield given;

14-boranyl-3,4-dimethoxy-6-methyl-5,6,7,8,14,15-hexahydro-benzo[c][1,3]dioxolo[4',5':4,5]benzo[1,2-g]azecine (883867-23-0) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 137 mg / H2O2; NaOH / tetrahydrofuran; H2O / Heating 2: 63 percent / pyridinium chlorochromate; NaOAc; 3A MS / CH2Cl2 / 2 h / 20 °C View Scheme

(-)-N-methylcanadine iodide (61774-67-2) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH / dimethylsulfoxide; benzene / 5 h / 20 °C 2: BH3*THF / tetrahydrofuran / 0.5 h / 20 °C 3: 137 mg / H2O2; NaOH / tetrahydrofuran; H2O / Heating 4: 63 percent / pyridinium chlorochromate; NaOAc; 3A MS / CH2Cl2 / 2 h / 20 °C View Scheme

(+/-)-trans-N-methyl-7,8,13,13a-tetrahydroberberinium iodide (18441-14-0, 26992-09-6, 60384-54-5, 60801-65-2, 61774-67-2, 62860-02-0, 62860-03-1, 92842-79-0, 100176-93-0) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaH / dimethylsulfoxide; benzene / 5 h / 20 °C 2: BH3*THF / tetrahydrofuran / 0.5 h / 20 °C 3: 137 mg / H2O2; NaOH / tetrahydrofuran; H2O / Heating 4: 63 percent / pyridinium chlorochromate; NaOAc; 3A MS / CH2Cl2 / 2 h / 20 °C View Scheme

3,4-dimethoxy-6-methyl-5,6,7,8-tetrahydro-11H-benzo[c][1,3]benzodioxolo[5,6-g]azecine (41759-47-1) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: BH3*THF / tetrahydrofuran / 0.5 h / 20 °C 2: 137 mg / H2O2; NaOH / tetrahydrofuran; H2O / Heating 3: 63 percent / pyridinium chlorochromate; NaOAc; 3A MS / CH2Cl2 / 2 h / 20 °C View Scheme

canadine (29074-38-2) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: acetone / 20 °C 2: NaH / dimethylsulfoxide; benzene / 5 h / 20 °C 3: BH3*THF / tetrahydrofuran / 0.5 h / 20 °C 4: 137 mg / H2O2; NaOH / tetrahydrofuran; H2O / Heating 5: 63 percent / pyridinium chlorochromate; NaOAc; 3A MS / CH2Cl2 / 2 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 180 mg / acetone / 6 h / 80 °C 2: AgCl / methanol / 1 h / Ambient temperature 3: 6.2 percent / H2O / 192 h / 24 °C / incorporation experiment on Macleaya cordata in Murashige and Skoog's medium View Scheme
Multi-step reaction with 4 steps 2: LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 2) NaBH4 / 1) MeOH, H2O, 10 min, 2) MeOH, H2O, room temp., 30 min 4: CH3COONa, pyridiniumchlorochromate / CH2Cl2 / 2 h View Scheme
Multi-step reaction with 3 steps 1: PhCO3H / CHCl3 2: K2CrO4 / H2O 3: methanol View Scheme

berberine chloride (633-65-8) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.45 g / NaBH4 / methanol / 1 h / Ambient temperature 2: 180 mg / acetone / 6 h / 80 °C 3: AgCl / methanol / 1 h / Ambient temperature 4: 6.2 percent / H2O / 192 h / 24 °C / incorporation experiment on Macleaya cordata in Murashige and Skoog's medium View Scheme

(+/-)-cis-N-methyl-7,8,13,13a-tetrahydroberberinium iodide (18441-14-0, 26992-09-6, 60384-54-5, 60801-65-2, 61774-67-2, 62860-02-0, 62860-03-1, 92842-79-0, 100176-93-0) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: AgCl / methanol / 1 h / Ambient temperature 2: 6.2 percent / H2O / 192 h / 24 °C / incorporation experiment on Macleaya cordata in Murashige and Skoog's medium View Scheme

(+/-)-14-Dihydro-nor-muramin (112333-56-9) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2) NaBH4 / 1) MeOH, H2O, 10 min, 2) MeOH, H2O, room temp., 30 min 2: CH3COONa, pyridiniumchlorochromate / CH2Cl2 / 2 h View Scheme

14-hydroxy-3,4-dimethoxy-5,6,7,8,14,15-hexahydrobenzo<1,3>dioxolo<4,5-k><3>benzazecine-6-carbonitrile (112333-20-7) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 2) NaBH4 / 1) MeOH, H2O, 10 min, 2) MeOH, H2O, room temp., 30 min 3: CH3COONa, pyridiniumchlorochromate / CH2Cl2 / 2 h View Scheme

9,10-dimethoxy-5,6,7,8,13,13a-hexahydro-2H-1,3-dioxolano[4,5-g]isoquinolino[3,2-a]isoquinoline-N-oxide (3906-36-3) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CrO4 / H2O 2: methanol View Scheme

9,10-dimethoxy-7-methyl-5,8,12b,13-tetrahydro-6H-[1,3]dioxolo[4'',5'':4,5]benzo[1',2':4,5]azepino[2,1-a]isoindolium; bromide (41759-43-7) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. NaOH 2: MCPBA / CHCl3; diethyl ether 3: aq. HCl / acetic acid View Scheme

(Z)-3,4-dimethoxy-6-methyl-5,6,7,8-tetrahydro-benzo[c][1,3]dioxolo[4',5':4,5]benzo[1,2-g]azecine (41759-45-9) → allocryptopine (485-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: MCPBA / CHCl3; diethyl ether 2: aq. HCl / acetic acid View Scheme

allocryptopine (485-91-6) → allocryptopine N-oxide (87264-52-6)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 24h; Ambient temperature;	86%

allocryptopine (485-91-6) → 13-oxoallocryptopine (15211-10-6)

Conditions	Yield
With mercury(II) diacetate In water; acetic acid at 75℃; for 4.5h;	41%

allocryptopine (485-91-6) → 12,13-dihydrochelerythrine (6880-91-7)

Conditions	Yield
In water at 24℃; for 168h; incorporation experiment on Macleaya cordata in Murashige and Skoog's medium;	33.4%
Multi-step reaction with 2 steps 1: 86 percent / m-chloroperbenzoic acid / CHCl3 / 24 h / Ambient temperature 2: 2 percent / 2.) NaBH4 / methanol / 1.) methanol, irradiation; 2.) methanol View Scheme
With recombinant Eschscholzia californica P450 CYP82N2v2; NADPH In aq. buffer at 30℃; pH=7.6; Kinetics; Enzymatic reaction;

allocryptopine (485-91-6) → 7,8-dimethoxy-2-methyl-3-(6-vinyl-benzo[1,3]dioxol-5-yl)-1,2-dihydro-isoquinoline (28332-37-8)

Conditions	Yield
(i) PCl3, (ii) KOH, MeOH; Multistep reaction;
Multi-step reaction with 2 steps 1: PCl3 2: KOH / methanol View Scheme

allocryptopine (485-91-6) → N-methyldihydroberberine chloride (26668-90-6)

Conditions	Yield
With phosphorus trichloride

trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) + allocryptopine (485-91-6) → N-methyldihydroberberine chloride (26668-90-6)

Conditions	Yield
α-allocryptopine;

sulfuric acid (7664-93-9) + allocryptopine (485-91-6) + sodium amalgam → dihydroallocryptopine

Conditions	Yield
α-allocryptopine;

allocryptopine (485-91-6) → C27H29NO8

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) PCl3, (ii) KOH, MeOH 2: benzene / Irradiation View Scheme

Upstream product

• 186581-53-3 diazomethane 
• 22047-92-3 9-demethylallocryptopine 
• 100176-55-4 9,10,13a-trimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline 
• 74-88-4 methyl iodide 
• 16211-68-0 (+/-)-cis-N-methyl-7,8,13,13a-tetrahydroberberinium chloride 
• 29074-38-2 canadine 
• 112333-20-7 14-hydroxy-3,4-dimethoxy-5,6,7,8,14,15-hexahydrobenzo<1,3>dioxolo<4,5-k><3>benzazecine-6-carbonitrile 
• 41759-45-9 (Z)-3,4-dimethoxy-6-methyl-5,6,7,8-tetrahydro-benzo[c][1,3]dioxolo[4',5':4,5]benzo[1,2-g]azecine 
• 41759-43-7 9,10-dimethoxy-7-methyl-5,8,12b,13-tetrahydro-6H-[1,3]dioxolo[4'',5'':4,5]benzo[1',2':4,5]azepino[2,1-a]isoindolium; bromide 
• 3906-36-3 9,10-dimethoxy-5,6,7,8,13,13a-hexahydro-2H-1,3-dioxolano[4,5-g]isoquinolino[3,2-a]isoquinoline-N-oxide 
• 112333-56-9 (+/-)-14-Dihydro-nor-muramin 
• 18441-14-0 (+/-)-cis-N-methyl-7,8,13,13a-tetrahydroberberinium iodide 
• 633-65-8 berberine chloride 
• 41759-47-1 3,4-dimethoxy-6-methyl-5,6,7,8-tetrahydro-11H-benzo[c][1,3]benzodioxolo[5,6-g]azecine 

Downstream Products

• 2086-83-1 berberine 

Relevant articles and documents

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An improved synthetic approach to protopines based on the sequential Hofmann elimination, hydroboration and oxidation of N-(arylmethyl)berbinium salts has been designed. By using berberine chloride as the starting material, this sequence of reactions has provided two new nonnatural protopines, N-benzyl-N-nordihydroallocriptopine and N-(p-methoxybenzyl)-N- nordihydroallocriptopine and the natural allocriptopine. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

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