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Home > Encyclopedia > Dithiazine

Dithiazine

Dithiazine structure

Dithiazine 

structure
  • CAS No:

    514-73-8

  • Formula:

    C23H23N2S2.I

  • Chemical Name:

    Dithiazine

  • Synonyms:

    Benzothiazolium,3-ethyl-2-[5-(3-ethyl-2(3H)-benzothiazolylidene)-1,3-pentadien-1-yl]-,iodide (1:1);3-Ethyl-2-[5-(3-ethyl-2-benzothiazolinylidene)-1,3-pentadienyl]benzothiazolium iodide;Benzothiazolium,3-ethyl-2-[5-(3-ethyl-2(3H)-benzothiazolylidene)-1,3-pentadienyl]-,iodide;Benzothiazolium,3-ethyl-2-[5-(3-ethyl-2-benzothiazolinylidene)-1,3-pentadienyl]-,iodide;Abminthic;Anelmid;[2-Bis(3-ethylbenzothiazolyl)]pentamethine cyanine iodide;Compound 01748;Delvex;3,3′-Diethylthiadicarbocyanine iodide;Dilombrin;Dilombrine;Dithiazanine iodide;Netocyd;Partel;Telmid;Telmide;Dithiazanin iodide;3,3′-Diethyl-2,2′-thiadicarbocyanine iodide;3,3′-Diethyldithiacarbodicyanine iodide;NK 136;Dithiazine;Anguifugan;Telmicid;Dejo;Omni-Passin;Diethylthiadicarbocyanine iodide;Eastman 7663;Dithiazine (dye);DTDC;Di-S-C2(5);DTDCI;3-Ethyl-2-[5-[3-ethyl-2(3H)-benzothiazolylidene]-1,3-pentadienyl]benzothiazolium iodide;SI 1964;3,3′-Diethylthiadicarbocyanine iodine;120103-39-1;1186-69-2;1986-69-2;51895-78-4

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

green crystalline powder


Dithiazanine iodide appears as green, needle-like crystals. Used as a veterinary anthelmintic, as a sensitizer for photographic emulsions and as an insecticides. Not registered as a pesticide in the U.S. (EPA, 1998)


Dithiazanine iodide appears as green, needle-like crystals. Used as a veterinary anthelmintic, as a sensitizer for photographic emulsions and as an insecticides. Not registered as a pesticide in the U.S. (EPA, 1998)|3-Ethyl-2-(5-(3-ethyl-2-benzothiazolinylidene)-1,3- pentadienyl)benzothiazolium. A benzothiazole that was formerly used as an antinematodal agent and is currently used as a fluorescent dye.

Dithiazine Basic Attributes

518.47700

518.03500

208-186-7

8OEC3RA07X

2811

DTXSID8022955

Dark greenish crystalline powder|Blue violet powder

29309099

Characteristics

65.29000

2.58000

Dithiazanine iodide appears as green, needle-like crystals. Used as a veterinary anthelmintic, as a sensitizer for photographic emulsions and as an insecticides. Not registered as a pesticide in the U.S. (EPA, 1998)

248 °C (decomp)

1.491

Practically insoluble in water

Poison room

LD50 intraperitoneal in mouse: 3mg/kg

Green needles from methanol; decomposes @ 248 °C

No rapid reaction with air. No rapid reaction with water.

Amines, Phosphines, and Pyridines

An amine, organosulfide. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Safety Information

II

6.1

UN 2811

3

R28;R36/37/38

S26-S28-S36/37-S45

DL7060000

T+

P261-P264-P301 + P310-P305 + P351 + P338

H300-H315-H319-H335

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Dithiazanine iodide is the only drug approved by the FDA in the USA for use as a heartworm microfilaricide in dogs.

When heated to decomposition, it emits toxic fumes of iodine, sulfur oxides, and nitrogen oxides. (EPA, 1998)

(Non-Specific -- Pesticide, Solid, n.o.s.) This material may burn but does not ignite readily. Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear self-contained, postive pressure if available, breathing apparatus and full protective clothing. (Non-Specific -- Pesticide, Solid, n.o.s.) Small fires: dry chemical, carbon dioxide, water spray or foam. Large fires: water spray, fog, or foam. Move container from fire area if you can do it without risk. (EPA, 1998)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

(Non-Specific -- Pesticide, Solid, n.o.s.) Do not touch spilled material; stop leak if you can do so without risk. Small spills: absorb with sand or other non-combustible absorbent material and place into containers for later disposal. Small dry spills: with clean shovel place material into clean, dry container and cover; move containers from spill area. Large spills: dike far ahead of spill for later disposal. (EPA, 1998)

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Dithiazanine iodide is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500/10,000 lbs.

Toxicity

LD50 Rat oral 165-192 mg/kg|LD50 Mouse oral 4-16 mg/kg

Drug Information

MEDICATION (VET): Dithiazanine has a broad spectrum of anthelmintic activity, being effective against not only heartworm microfilariae but also the common intestinal nematodes of dogs (hookworms, ascarids, whipworms), Strongyloides stercoralis, and perhaps Spirocerca lupi.|MEDICATION (VET): Dithiazanine is ... administered orally immediately after or during feeding.|MEDICATION (VET): Since vomiting and diarrhea are frequent side effects, the lowest dose (6.6-11 mg/kg) is recommended daily for 7 days. Splitting the daily dose and giving 3.3 mg/kg twice daily at feeding helps to reduce occurrence of side effects. If the animal is positive for circulating microfilariae after 7 days, the dose may be increased to 11 mg/kg daily until the blood is negative for microfilariae or for no longer than 10 days.|Anthelmintic (Nematodes)

It is considered a toxic anthelmintic.|... vomiting and diarrhea are frequent side effects ...|A low percentage of dogs have been killed by the 20 mg/kg/day dose in as few as 3 days. Perhaps these were animals with hepatorenal disease, since dithiazanine is toxic to both organs.

Dogs are reported to tolerate a single high dose of 200 mg/kg, but repeated daily doses of 12-20 mg/kg/day for 3-7 days are often poorly tolerated.

Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags. (See all compounds classified as Fluorescent Dyes.)|Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)

Absorption of this blue violet compound from the intestinal tract is minimal but is sufficient to cause a faint blue coloration of tissues. Since most of the drug remains unabsorbed in ingesta, feces and vomitus of dogs are blue green to purple in color.

The means by which dithiazanine clears circulating microfilariae from the blood is not known. They evidently lose motility, become trapped in capillary beds, & are eventually phagocytized by host cells ... The biochemical basis of action of dithiazanine on helminths has been only partially determined. Studies with canine whipworms indicate that the drug causes an irreversible inhibition of glucose absorption, thus resulting in marked reduction in free glucose and consequent depletion in energy-rich phosphate bonds. Whether these physiologic changes also occur in heartworm microfilariae exposed to the drug is not known.

Highly toxic by mouth. (Non-Specific -- Pesticide, Solid, n.o.s.) Poisonous if swallowed, or if dust is inhaled. (EPA, 1998)

Ingestion is a route of entry.Move victim to fresh air; call emergency medical care. Remove and isolate contaminated clothing and shoes at the site. In case of contact with material, immediately flush skin or eyes with running water for at least 15 minutes. (EPA, 1998)

Two people pressing powdered drug into tablets were exposed to enough dust in the course of a week to develop faint blue discoloration of the conjunctiva and slight hyperemia and swelling of the plica semilunaris, but with a change in occupation this all cleared in 10 days.

3,3' Diethylthiadicarbocyanine

Dithiazine Use and Manufacturing

Methods of Manufacturing

/Prepared/ ... from 1-methylbenzothiazole ethiodide and beta-(ethylmercapto)acrolein diethyl acetal: Kendall, Edwards, US Patent 2,412,815 (1946 to Ilford).

Uses

Sensitizer for photographic emulsions.

... available as a powder or tablet

Benzothiazolium, 3-ethyl-2-[5-(3-ethyl-2(3H)-benzothiazolylidene)-1,3-pentadien-1-yl]-, iodide (1:1): ACTIVE|... is a cyanine dye

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Computed Properties

Molecular Weight:518.5
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:518.03474
Monoisotopic Mass:518.03474
Topological Polar Surface Area:60.7
Heavy Atom Count:28
Complexity:537
Undefined Bond Stereocenter Count:3
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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