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Name	DISTAMYCIN A HYDROCHLORIDE	EINECS	229-505-6
CAS No.	6576-51-8	Density	N/A
PSA	181.06000	LogP	3.67870
Solubility	CLEAR YELLOW TO GREEN SOLUTION AT 20MG/ML IN ETHANOL	Melting Point	184-187° (Arcamone, 1967). Also reported as 189-193° from ethanol-ethyl acetate (Bialer)
Formula	C22H27 N9 O4 . Cl H	Boiling Point	715.4 °C at 760 mmHg
Molecular Weight	517.975	Flash Point	386.4 °C
Transport Information	N/A	Appearance	YELLOW TO YELLOW WITH A BROWN CAST POWDER
Safety	Poison by intraperitoneal and intravenous routes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NO_x and HCl.	Risk Codes	43
Molecular Structure		Hazard Symbols	Xi
Synonyms	1H-Pyrrole-2-carboxamide,N-[5-[[(3-amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl]-4-[[[4-(formylamino)-1-methyl-1H-pyrrol-2-yl]carbonyl]amino]-1-methyl-,monohydrochloride (9CI); N,4':N',4''-Ter[pyrrole-2-carboxamide],N''-(2-amidinoethyl)-4-formamido-1,1',1''-trimethyl-, hydrochloride (7CI);N,4':N',4''-Ter[pyrrole-2-carboxamide],N''-(2-amidinoethyl)-4-formamido-1,1',1''-trimethyl-, monohydrochloride (8CI);Distamycin A hydrochloride; Distamycin hydrochloride; MEN 10399; Stallimycinhydrochloride	Article Data	3

DISTAMYCIN A HYDROCHLORIDE Synthetic route

: 77727-43-6
N-Succinimidyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate

: 77152-88-6
(1-amino-3-ammoniopropylidene)ammonium dihydrobromide

: 6576-51-8
distamycin A hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydrogencarbonate In 1,4-dioxane; water 1.) 15 min, ice-cooled, 2.) room temperature, overnight; Yield given;

: 3786-88-7
1-methyl-4-<1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido>pyrrole-2-carboxamidopropionamidine hydrochloride

: 3197-61-3
N-formylimidazole

: 6576-51-8
distamycin A hydrochloride

Conditions

Conditions	Yield
In tetrahydrofuran; methanol at -40℃; for 0.5h; Yield given;

: 6973-60-0
1-Methyl-2-pyrrolecarboxylic acid

: 6576-51-8
distamycin A hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 43 percent / 1.) 70percent nitric acid, acetic anhydride / 1.) a) -15 deg C, 0.5 h, b) RT, 20 min 2: SOCl2 / tetrahydrofuran / 0.08 h / Heating 3: Hunig's base / tetrahydrofuran / -20 - 20 °C 4: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C 5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 8: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme
Multi-step reaction with 8 steps 1: 43 percent / 1.) 70percent nitric acid, acetic anhydride / 1.) a) -15 deg C, 0.5 h, b) RT, 20 min 2: SOCl2 / tetrahydrofuran / 0.08 h / Heating 3: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min 4: 95 percent / NaOH / H2O; ethanol / Heating 5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 8: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 43 percent / 1.) 70percent nitric acid, acetic anhydride / 1.) a) -15 deg C, 0.5 h, b) RT, 20 min
2: SOCl2 / tetrahydrofuran / 0.08 h / Heating
3: Hunig's base / tetrahydrofuran / -20 - 20 °C
4: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C
5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
8: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme

Multi-step reaction with 8 steps
1: 43 percent / 1.) 70percent nitric acid, acetic anhydride / 1.) a) -15 deg C, 0.5 h, b) RT, 20 min
2: SOCl2 / tetrahydrofuran / 0.08 h / Heating
3: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min
4: 95 percent / NaOH / H2O; ethanol / Heating
5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
8: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme

: 13138-78-8
1-methyl-4-nitro-pyrrol-2-carboxylic acid

: 6576-51-8
distamycin A hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: SOCl2 / tetrahydrofuran / 0.08 h / Heating 2: Hunig's base / tetrahydrofuran / -20 - 20 °C 3: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C 4: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 5: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 6: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 7: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme
Multi-step reaction with 7 steps 1: SOCl2 / tetrahydrofuran / 0.08 h / Heating 2: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min 3: 95 percent / NaOH / H2O; ethanol / Heating 4: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 5: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 6: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 7: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme
Multi-step reaction with 8 steps 1: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 2: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 3: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 4: TFA / CH2Cl2 5: EDC / dimethylformamide / 40 °C 6: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 7: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 8: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

: 97950-76-0
1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxylic acid

: 6576-51-8
distamycin A hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 2: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 3: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 4: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

: 69910-20-9
methyl 1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carbonate

: 6576-51-8
distamycin A hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / NaOH / H2O; ethanol / Heating 2: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 3: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 4: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 5: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

: 28494-51-1
1-methyl-4-nitro-1H-pyrrole-2-carbonyl chloride

: 6576-51-8
distamycin A hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: Hunig's base / tetrahydrofuran / -20 - 20 °C 2: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C 3: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 4: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 5: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 6: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme
Multi-step reaction with 6 steps 1: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min 2: 95 percent / NaOH / H2O; ethanol / Heating 3: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 4: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 5: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 6: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: Hunig's base / tetrahydrofuran / -20 - 20 °C
2: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C
3: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
4: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
5: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
6: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme

Multi-step reaction with 6 steps
1: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min
2: 95 percent / NaOH / H2O; ethanol / Heating
3: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
4: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
5: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
6: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme

: 13138-76-6
1-methyl-4-nitropyrrole-2-carboxylic acid methyl ester

: 6576-51-8
distamycin A hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 92 percent / aq. NaOH / Heating 2: SOCl2 / tetrahydrofuran / 0.08 h / Heating 3: Hunig's base / tetrahydrofuran / -20 - 20 °C 4: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C 5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 8: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme
Multi-step reaction with 8 steps 1: 92 percent / aq. NaOH / Heating 2: SOCl2 / tetrahydrofuran / 0.08 h / Heating 3: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min 4: 95 percent / NaOH / H2O; ethanol / Heating 5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 8: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 92 percent / aq. NaOH / Heating
2: SOCl2 / tetrahydrofuran / 0.08 h / Heating
3: Hunig's base / tetrahydrofuran / -20 - 20 °C
4: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C
5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
8: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme

Multi-step reaction with 8 steps
1: 92 percent / aq. NaOH / Heating
2: SOCl2 / tetrahydrofuran / 0.08 h / Heating
3: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min
4: 95 percent / NaOH / H2O; ethanol / Heating
5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
8: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme

: 3185-95-3
1-methyl-4-nitro-1H-pyrrole-2-carboxylic acid (2-cyanoethyl)amide

: 6576-51-8
distamycin A hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C 2: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 3: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 4: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 5: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C
2: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature
3: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT
4: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C
5: methanol; tetrahydrofuran / 0.5 h / -40 °C
View Scheme

: 2522-28-3
3-<1-methyl-4-<1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxamido>pyrrole-2-carboxamido>propionitrile

: 6576-51-8
distamycin A hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 2: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 3: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

DISTAMYCIN A HYDROCHLORIDE Chemical Properties

MF: C₂₂H₂₇N₉O_4.HCl
MW: 517.97
EINECS: 229-505-6
Following is the molecular structure of DISTAMYCIN A HYDROCHLORIDE:

DISTAMYCIN A HYDROCHLORIDE Toxicity Data With Reference

1.	dni-mus:lym 1900 nmol/L	CBINA8 Chemico-Biological Interactions. 8 (1974),183.
2.	oms-mus:lym 3200 nmol/L	CBINA8 Chemico-Biological Interactions. 8 (1974),183.
3.	dnd-mam:lym 200 µmol/	EJBCAI European Journal of Biochemistry. 26 (1972),81.
4.	ipr-rat LD50:169 mg/kg	MDACAP Medicamentos de Actualidad. 13 (1977),319.
5.	ipr-mus LD50:160 mg/kg	MDACAP Medicamentos de Actualidad. 13 (1977),319.
6.	ivn-mus LD50:75 mg/kg	MEIEDD Merck Index. 11 (1989),1383.

RTECS :WZ7110000

DISTAMYCIN A HYDROCHLORIDE Safety Profile

Poison by intraperitoneal and intravenous routes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NO_x and HCl.

Hazard Codes : Xi (Irritant)
Risk Statements: 43 (May cause sensitization by skin contact)
Safety Statements : 36/37 (Wear suitable protective clothing and gloves)
WGK Germany: 3

DISTAMYCIN A HYDROCHLORIDE Specification

storage temp:?20°C

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